WO1998014452A1 - Heterocycle-fused pyrimidinone derivatives and herbicides - Google Patents

Abstract

Compounds represented by general formula (I) and salts thereof; and herbicides containing them, wherein Rf is C1-C4 haloalkyl; X∩Y is N=N, CH=N or the like; A is nitrogen or CH; Z is oxygen or sulfur; Rg is hydrogen, halogeno or the like; and R1, R2, R3, R4 and R5 are each independently hydrogen, halogeno, nitro, cyano or the like.

Description

 Description Heterocyclic fused pyrimidinone derivatives and herbicides

[Technical field to which the invention belongs]

 The present invention relates to a herbicide containing a novel heterocyclic fused pyrimidinone derivative as an active ingredient.

 [Conventional technology and issues]

 Many herbicides have been used to protect important crops such as rice, soybeans, wheat, corn, potatoes and beets from weed damage, and to increase the productivity of these important crops. Existing drugs do not fulfill all required functions.

 It has never been known that the compounds of the present invention having a haloalkyl group at the 6-position of the pyrimidinone ring, a heterocyclic ring condensed at the 1- and 2-positions, and a substituted phenyl group at the 3-position exhibit herbicidal action. Not been.

 [Means to solve the problem]

 The present inventors have conducted intensive studies on the herbicidal activity of the novel heterocyclic fused pyrimidinone derivative, and as a result, have found that the compound of the present invention represented by the following formula has an excellent herbicidal activity, and completed the present invention. Was.

 That is, the present invention provides a compound of formula (I):

〔式中、 R f は d — C ハロアルキル基を表わし、

[Wherein, R f represents a d-C haloalkyl group;

 X and Y each independently represent a carbon, nitrogen, oxygen or sulfur atom;

X~Y is N = N, C (R a ) = C (R b) (R a, R b it it independently water atom, halogen atom, C -! C ₄ alkyl group, d - C 4 alkoxy, d - C ₄ haloalkyl group, a hydroxyl group, an amino group, a mercapto group, a carboxyl group, human mud Kishimechiru group, forces Rubamoiru group, a formyl group, d - C ₄ alkyl group, C 1 - C 4 alkoxycarbonyl group, C ₄ alkylamino, C ₂ —Cs alkenyl, C ₂ —C ₆ alkynyl, C ₄ alkylmercapto, C ₃ -C alkenylamino, C ₃ —C alkynylamino, benzyloxy A benzylamino group, a C ₄ alkylsulfinyl group, a c ₄ alkylsulfonyl group, a pyridyl group or an optionally substituted phenyl (SP 1) group (optionally substituted phenyl (SP 1) is a halogen atom, c -! C ₄ Alkyl group,

A C 1 -C 4 alkoxy group, —C 4 haloalkyl group, —C 4 haloalkoxy group or a phenyl group which may be substituted by a phenyl group). )

C (R a) 2 N (R a has the same meaning as described above.),

 N = C (Ra) (Ra represents the same meaning as described above.),

 CH (Ra) CH (Rb) (Ra and Rb have the same meanings as described above.),

CH ₂ CH ₂ CH ₂ , CH = CHCH ₂ , CH ₂ CH = CH,

 NHC (Ra) Rb (Ra and Rb represent the same meaning as described above.)

 C (Ra) (Rb) NH (Ra and Rb have the same meanings as described above),

C (= 0) C (= 0), CH ₂ C (= 0) NH, CH ₂ CH ₂ S 0 ₂ ,

 C (= 0) CH (Ra) (Ra represents the same meaning as described above.),

 CH (R a) C (= 0) (R a has the same meaning as described above.)

 C (= 0) NH, C (= S) NH, NH C (= 0), NHC (= S),

 C (= ◦) C (Ra) = N (Ra represents the same meaning as described above.),

C (= 0) C (Ra) = C (Rb) (Ra and Rb represent the same meaning as described above.) C (R a) = C (R b) C (= 0) (R a and R b have the same meanings as described above.)

 N = C (Ra) C (= 0) (Ra represents the same meaning as described above.)

CH (Ra) C (= 0) NH (Ra represents the same meaning as described above),

C (= 0) N (R a) C (= 0) (R a has the same meaning as described above.), C (R a) = NC (= 0) (R a has the same meaning as described above.) ),

C (R a) 0 (R a has the same meaning as described above.),

C (= 〇) represents 0, 0 C (= 0) or S C (= 0),

 A represents a nitrogen atom or CH,

Z is an oxygen atom, a sulfur atom, NR c (R c is a hydrogen atom, d—C ₄ alkyl group, C—C ₄ alkoxycarbonyl group, 1 C ₄ alkoxycarbonylmethyl group, or optionally substituted phenyl (SP 2) Group (optionally substituted phenyl (SP 2) group is a halogen atom, —C ₄ alkyl group, —C ₄ alkoxy group or C! -C 1 -C haloalkyl group. A NNHR c (R c has the same meaning as described above).

R g is a hydrogen atom, a halogen atom, a cyano group, a d—C ₄ alkoxycarbonyl group, a C—C ₆ alkenyl group, a Cs—C ₆ alkynyl group or a C! — Represents a C ₄ alkyl group,

R1, R2, R3, R4 and R5 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a thiocarbamoyl group, a carbamoyl group, a mercapto group, a hydroxyl group, an amino group , Formyl, carboxyl, vinyl, ethynyl, trimethylsilylethynyl, cyanomethyl, sulfamoyl, -C ₈ alkyl, C ₃ -C ₈ alkenyl, C i -C alkylsulfonyl, C ₃ —C ₈ alkynyl group, C ₃ —C ₈ cycloalkyl group, C i —C ₄ haloalkyl group,

C—C nodoxyalkenyl group, C 3 —C ₈ haloalkynyl group, Cl—C 4 acyl group,

C t—C ₄ alkoxy (d—Cz) alkyl group, CC 4 alkylsulfinyl group, optionally substituted phenyl (SP 3) group (however, the optionally substituted phenyl (SP 3) group halogen atom, C i - C ₄ haloalkyl group, -! C ₄ Al kill group, one C 4 alkoxy groups, C one C ₄ haloalkoxy group, methanesulfonic two Le group, C! One C ₄ alkoxycarbonyl group, a nitro group, arsenate Dorokishiru group, an amino group, Shiano group, One _{0- CH (CH 3) C 02} (d- C 4 alkyl) group or a 0- CH

2 represents a phenyl group which may be substituted by a C 02 (C i -C ₄ alkyl) group. ), — Q— (optionally substituted phenyl (SP 3) group) group (Q may be saturated or unsaturated, branched and may be substituted by a halogen atom.

— Represents an alkylene chain of C _{6, and} the optionally substituted phenyl (SP 3) group has the same meaning as described above. ), — 0— Q— (optionally substituted phenyl (SP 3) group) group (Q and the optionally substituted phenyl (SP 3) group have the same meanings as described above), — S—Q— (optionally substituted phenyl (SP 3) group) group (Q and optionally substituted phenyl (SP 3) group have the same meanings as described above.), One NH—Q — (Optionally substituted phenyl (SP 3) group) group (Q and the optionally substituted phenyl (SP 3) group have the same meanings as described above.), — 0— (substituted Phenyl (SP 3) group (optionally substituted phenyl (SP 3) group has the same meaning as described above), — S— (optionally substituted phenyl (SP 3) group) Group) group (optionally substituted phenyl (SP 3) group has the same meaning as described above.), One NH— (substituted Te Moyoi Fuweniru (SP 3) group) group (optionally substituted phenyl (SP 3) group represents the same meaning as defined above.)

-0-R 11 (R 1 UiC) —C ₈ alkyl group, C ₃ —C ₈ cycloalkyl group, C 3 —C ₈ cycloalkyl (C t—C) alkyl group, C ₃ —C ₈ alkenyl group, C

Three to C ₈ alkynyl group, C 3 -C ₈ haloalkenyl group, C 1 over C 4 haloalkyl Cal Boniru group, C ₃ - C ₈ Bruno, mouth alkynyl group, C i -c ₄ haloalkyl group, d - c ₄ § Lucoxy (C, —c ₄ ) represents an alkyl group, a cyanomethyl group or a d—c ₄ acyl group. ), One NH—R l 1 (R 11 has the same meaning as described above.)), One S—R 11 1 (R 11 has the same meaning as described above.), —CON (C! — C ₄ alkyl) ₂ groups, — CONH (C! — C ₄ alkyl) group, — C0 ₂ R 12 (R 12 is d — C ₈ alkyl group, C ₃ — C ₈ cycloalkyl group, C ₃ -C ₈ alkenyl group, C ₃ - C ₈ Al Kiniru group, optionally substituted Fuweniru (SP 3) group (optionally substituted Fuweniru (SP 3) group represents the same meaning as defined above.) , — Q— (substituted Phenyl (SP 3) group (Q and optionally substituted phenyl (SP 3) group have the same meaning as described above), oxetane-3-yl group, C! —C ₄ Represents an alkoxycarbonylmethyl group or a (C! -CAalkyl) 2 amino group. ), Single CONHR 1 2 (R 1 2 represents the same meanings as defined above;..), One _{Q- C 0 2 R 1 2 (} Q and R 1 2 are representative of the same meanings as defined above), - 0 — Q—C0 ₂ R 12 (Q and R 12 have the same meanings as described above), and one NH—Q—C 0 ₂ R 12 (Q and R 12 have the same meanings as above.) ;), — S— Q— C0 ₂ R 12 (Q and R 12 have the same meanings as above.;), — NH S 0 ₂ R 13 (R 13 is C i —C ₈ alkyl —C ₄ —C ₄ haloalkyl group, C ₃ —C ₆ cycloalkyl group, C 3 —C ₈ alkenyl group, C ₃ —C ₈ alkynyl group, benzyl group or phenyl group.), —N (S 0 ₂ R 13) ₂ (R 13 has the same meaning as described above.), -CO NH SO 2 RI 4 (R 14 is a d_C ₄ alkyl group or a C! C ₄ peralkylalkyl group). ), —N (R 15) S〇 ₂ R 13 (R 13 has the same meaning as described above, and R 15 is ! C one C ₆ alkyl group, C 3 - C 8 alkenyl group, C 3 - C 8 Al Kiniru group, CC 4 haloalkyl group, C 3- C 8 haloalkenyl, C ₃ - C ₈ halo alkynyl group, C! — C ₆ acyl group, formyl group, cyano (C! —CA) alkyl group, C 1 — C 4 alkoxy (d-C ₄ ) alkyl group, d — C ₄ alkoxycarbonyl group or one C (= 0) (substituted which may be Fuweniru (SP 3) group) group (which may be substituted Fuweniru (SP 3) group represents represents) the same meaning as _{above), -.. NHC0 2 R} 1 6 ( R 16 is a C! —C ₆ alkyl group, C ₃ —C ₈ alkenyl group, C ₃ —C ₈ alkynyl group, d—C 4 haloalkyl group, phenyl group or 1 Q— (optionally substituted Phenyl (SP 3) group (Q and the phenyl (SP 3) group which may be substituted have the same meaning as described above. ). ), -O-CO 2 R 16 (R 16 has the same meaning as described above.):), N (R 15) C 0 ₂ R 16 (R 15, R 16 are the same as described above) ;), — N (R 15) R 11 (R 11 and R 15 have the same meanings as described above.), 2,3-epoxy—2-methylpropyl group, 2 —Methyl-2-propenyl group, 1,3-dioxolan-2-yl group or 1,3-dioxane-12-yl group,

R 2 and R 3 form a heterocycle as shown in formulas (a), (b) and (c) May be

Note that R f, R g, A, X, Y, Z, R l, R in the equations (a), (b) and (c)

4 and R 5 represent the same meaning as described above,

! ^ は is ^ — C ₆ alkyl group, C ₃ — C ₈ alkenyl group, C ₃ — C ₈ alkynyl group, C i — C haloalkyl group, CC haloalkenyl group, C ₃ — C ₈ haloalkynyl group, 1 C _6- acyl group, formyl group, benzoyl group, d—C ₆ haloalkylcarbonyl group, phenacyl group, C ₃ —C ₈ cycloalkyl (d-C ₄ ) alkyl group, d—C ₄ alkoxy (C t-C ₄ ) alkyl _{group, - Q- C 0 2 (C} - CO alkyl group (wherein, Q represents the same meaning as above) -. Q-CN group (wherein, Q Represents the same meaning as described above. Or one Q— (optionally substituted phenyl (SP 3) group) group (wherein Q and optionally substituted phenyl (SP 3) group have the same meanings as described above).

 However, when these compounds include optical isomers, diastereomers, and geometric isomers, both the respective mixtures and the isolated isomers are included. ] It is a novel heterocyclic fused pyrimidinone derivative (henceforth a compound of this invention) shown by these, and a herbicide characterized by containing them as an active ingredient.

 [Embodiment of the invention]

In equation (I),

R f can be CF ₃ , CF ₂ C 1, CF ₂ H, CFC 1 H, CF ₃ CF ₂ , or F ₂ C 1 CF ₂ is preferable, and CF ₃ is preferable.

The R g H, F, C l , B r, C≡N, C_〇 _{2 Me, CH 2 CH = CH} 2, CH 2 C three CH, Me, E t, P r, iso- P r or B u, and preferably H or F.

The Z an oxygen atom, a sulfur atom, NH, NMe, NE t, NP r, NBu, N- tert- Bu, NC0 2 Me, NC0 2 E t, NCH 2 C0 2 Me, NCH2CO2 E t, NPh, N- (4—CI-Phenyl), N- (3-Cl-Pheny1), N- (2-CI—Phenyl), NNHMe, NNHEt, NNHPr, NNHBu, NNH—tert-Bu , NNH - (4 one CI one _{Phe ny l), NNH 2,} NNH- (3 - CI- Phe ny l), NNH- (2 -C l -Phe nyl), NNH CH2C 0 2 Me, NNH CH2C O2E t , NNHPh, NNH C 〇 ₂ Me or NNHC0 ₂ E t and the like, preferably an oxygen atom.

A includes CH or N, and preferably N.

X to Y are N = N, CH = N, N = CH, C (CI) = N, N = C (CI), C (Br), N = N (Cr), CH = CH , C (CI) = CH, CH = C (CI), C (Br) = CH, CH = C (Br), C (Me) = CH, CH = C

(Me), N = C (Me), N = C (Ph), C (Me) = N, C (Ph) = N, C (Et) = CH, CH = C (Et), C (P r) = CH, CH = C (P r), CH2CH2, CHzCH (Me), CH (Me) CH 2, CH2CH (E t), CH

_{(E t) CH 2, CH2CH} (P r), CH (P r) CH 2, CH2CH2CH2, CH = CHCH 2, CH 2 CH = CH, CH2C (= 〇) NH, CH2CH2S O2, C

(= 0) C (= 0), CH2C (= 0), C (= 〇) NH, C (= S) NH, NH C (= (), NH C (= S), C (= 〇) CH = N, C (= 0) CH = CH, CH2 CHC (= 0), N = CHC (= 〇), CH2C (= 0) NH, C (= 0) NHC (= 0), C (= 0) N (Me) C (= 0), CH = NC (= 0), CH ₂ 〇, C (= 0) 0, 0 C (= ◦), SC (= 0) or C (= 0) S CH = N, N = CH, CH = CH, CH2CH2, C (CHa) = CH, C

(C 2H 5) = CH, CH = C (CH 3), CH = C (C2H5), CH (CH 3) CH 2, CH (C 2H 5) CH 2, CH2CH (CH 3), CH2CH (C 2 H 5), C (C H2CH2CH3 ) two CH or _{CH = C (CH 2 CH 2} CH 3,) and the like, preferably is CH = CH in further.

R 1 includes H, Cl, F, Br, or I, and preferably H, Cl, or F.

R5 includes H, Cl, F or Br, and preferably H.

As R 2 is H, C l, F, B r, I, CN, C SNH 2, C ONH2, C≡CH, C≡CS iMe 3, CH = CH 2, Me, E t, P r, iso- Pr, 0—Me, 0-Et, S0 ₂ NH ₂ , 〇 CH ₂ C0 ₂ Me, 0 CH ₂ C O2E t, 0 CH2CH2C 0 ₂ Et, CF ₃ , CF 2 CF 3, CF ₂ C 1 _{, CF 2 H, CF 3 0} , NO2, HCF 2 0 C 1 CH 2, B r CH 2, SMe, S 0 2 Me,

_{0H, SH, NH 2, CHO} , C0 2 H, C0 2 Me, C O2E t, CH 2 CN, NH Me, NMe 2, O CH 2 OMe, O CH 2 Ph, O CH2 (4 -C l -phe ny 1), 0 CH ₂ (4— B r— pheny l), 〇 CH ₂ (4-Me— phe ny l), 〇 CH ₂ (4-C 1-2-(0 CH (Me) C〇 ₂ Me )-he ny l), 0 CH ₂ (4 -Me-2-(〇CH (Me) C〇 ₂ Me)-he ny l), 〇 CH ₂ (4-CI 1 2-(0 CH (Me) C 0 ₂ E t)-he nl), 0 CH 2 (4 -Me-2-(0 CH (Me) C O2E t)-he nl), NHCH ₂ Ph, NH CH ₂ (4-CI-phe ny l), NH C H2 (4-Br-phe ny l), NH CH2 (4-Me-phe ny l), NH CH ₂ (4-CI-2-(0 CH (Me) C〇 ₂ Me) -phe ny l), NH CH2 (4-Me-2-(0 CH (Me) C0 ₂ Me) -phe ny l), S CH ₂ Ph, S CH ₂ (4-C l -ph e ny l) , S CH2 (4 -B r-phe ny l), S CH ₂ (4 -Me -phe ny 1), S CH ₂ (4-CI 1 2-(0 CH (Me) C 0 ₂ Me)- pheny 1), SCH ₂ (4 -Me-2-(〇 CH (Me) C 02M e) -phe ny l), 0 CH (Me) C〇 ₂ Me, OCH (Me) C0 ₂ Et, NHCH ₂ C_〇 ₂ Me, N HCH ₂ C_〇 ₂ E t, include S CH ₂ C0 ₂ Me or S CH ₂ C0 ₂ E t, is favored properly F, C l, B r, I, CN, N 0 2 or CSNH _2, and the like.

The R 3, H, C l, F, B r, I, CH_〇, C_〇 _{2 H, C 0 NH 2,} SO 2 C 1, C0Me, SH, 0H, NH 2, N 02, CN, Phe ny l, Me, E tヽP r, iso- P r, Bu , sec- Bu, iso- Bu, tert- Bu, P n, neo- P ntert- P n x cyclo- P r, cyclo- Bu, cyclo—Pn, cyclo—Hex, CH ₂ CH = CH ₂ , CH (Me) CH = CH ₂ , CH ₂ C≡CH, CH (Me) C≡CH, 0-1 Me, 0—Et, 0-1 iso—Pr, 0—Pr, 0—Bu, 0—sec—Bu, 0—iso—Bu, 0—cyclo—Pn, 0—cyclo—Pr, 0—cyclo—Hex, 0—neo—Pn , Ot ert -Pn, 0- Pn, 0- He x, 0- He p, 0- O ct, O CH 2 CH = CH 2, O CH (Me) CH = CH 2, 0 C (Me) 2 CH = CH ₂ , 0 CH ₂ C≡CH, O CH (Me) C 3 CH, 0 C (Me) ₂ C≡CH, 0 CH2C H = C (CI) H, 0 CH2C (CI) = CH ₂ , O CH ₂ CF ₃ , 0 CH2CH2O Me, O CH ₂ CH ₂ OE t, 0 CH2OM e, 0 CH ₂ 0E t, O CHz-cycl o- P r, OCH ₂ CN, OC_〇_Me, OC_〇_E t, OC_〇_P r, 0C0- iso one P r, 0 CH2C (Me) two _{CH 2, 0- iso- Pn, S-} Me, S — Et, S—iso—Pr, S—Pr, S—Bu, S—sec—Bu, S—iso—Bu, S—cyclo—Pn, S—cycl 'o—Pr, S—cyclo - H ex, S - ne o- Pn, St ert -Pn, S- Pn, S- He x, S- He p, S - 〇 ct, S CH ₂ CH two _{CH 2, S CH (Me)} CH = CH ₂ , SC (Me) 2 CH = CH ₂ , S CH ₂ C≡CH, S CH (Me) C3 CH, SC (Me) ₂ C3 CH, S CH ₂ CH = C (CI) H, S CH2C (CI) = CH2, S CH 2 CF 3, S CH 2 CH 2 _{〇_Me, S CH 2 CH 2 OE t} , S CH 2 〇_Me, S CH ₂ 〇_E t, S CH2- cyclo- P r, S CH ₂ CN, NH—Me, NH—Et, NH—iso—Pr, NH—Pr, NH—Bu, NH—sec—Bu, NH—iso—Bu, NH—cyclo—Pn, NH—cyclo — Pr, NH—cyclo—Hex, NH—neo—Pn, NH-tert-Pn, NH—Pn, NH—Hex, NH—Hep, NH—Oct, NHCH ₂ CH = CH ₂ , NHCH (Me) CH = CH ₂ , NH C (Me) ₂ CH = CH ₂ , NH _{CH 2 C≡CH, NHCH (Me)} C three _{CH, NH C (Me) 2} C≡CH, NH CH 2 CH = C (CI) H, NH CH2C (CI) = CH 2, NHCH 2 CF 3, NHCH _{2 CH 2 OMe, NHCH2CH2OE t,} NHCH 2OM e, NH CH2O E t, NH CH 2 - cyc 1 o- P r, NH CH2CN, C 0 2 Me, C O2E t, C0 2 - iso- P r, C 0 _{zP r, C0 2 - cyclo- P} r, C 02B u, C0 2 - sec- Bu, C0 2 - iso- Bu, C 02- tert one _{Bu, C 0 2 - cyc 1} o- B u, C0 2 Pn _{, C 0 2 - cyc 1 o-} P n, CO 2 Pn, C0 2 -ne o-Pn, C0 2 - tert -Pn, C0 2 - H ex, C 02- cyclo- H ex, C0 2 - He p _{, C0 2 -O ct, C 0} 2 N (Me) 2, CO 2N (E t) 2, C0 2 CH 2 C0 2 Me, C_〇 ₂ CH ₂ C0 ₂ E t, C_〇 ₂ CH ₂ C 0 ₂ P r, C0 ₂ Ph, C0 ₂ CH ₂ Ph, CONHE t, CONHP r, CONHBu, CONH- tert-Bu, CONHPh, CONHCH ₂ Ph, CH ₂ CH (C 1) C0 ₂ Me, CH2CH (CI) C O2E t, CH ₂ CH ₂ C0 ₂ Me, CH2CH ₂ CH ₂ C0 ₂ Me, CH2C 0 ₂ Me, CH = CHC0 ₂ Me, CH = CHC0 ₂ E t, O CH ₂ C0 ₂ Me, 0 CH 2 C 0 ₂ E t, O CH ₂ C0 ₂ Pr, 0 CH2C O2B u, 0 C H2C O 2P n, 0 CH 2 CO 2H e, 〇 CH ₂ C〇 ₂ — cyc 1 o— P n, 〇 CH ₂ C〇 ₂ — iso—P r, 0 CH ₂ C〇 ₂ CH ₂ P h , O CH (Me) C0 ₂ Me, 0 CH (Me) CO 2E t, O CH (Me), C〇 ₂ Pr, O CH (Me) CO 2-iso—P r, O CH (Me) C0 _{2 Pn, OCH (Me) C0} 2 - cycl oP n, S CH 2 C0 2 Me, S CH 2C O 2E t, S CH2 CO 2P r, S CH2C O2B u, SC H2C O2P n, SC H2C 0 2 H ex , S CH2C O 2 — cyclo— Pn, SC H2C O 2-iso -P r, SC H2C O 2C H2P h, S CH (Me) C O2M e, S CH (Me) C〇 ₂ Et, S CH ( _{Me) C0 2 P r, S} CH (Me) CO 2 - iso- P r, S CH (Me) C_〇 _{2 Pn, S CH (Me)} C0 2 - cyclo - Pn, NH C H2 CQ 2 Me, NH C H2C O2E t, NH C H2C O2P r, NH C H2C O2B U, NH C H2 CO 2P n, NH CH 2 CO 2H e, NHCH 2 C_〇 ₂ one _{cyclo- Pn, NHCH 2 C 0 2} - iso - P r, NHCH 2 C 02 CH 2 P h NHCH (Me) C0 2 Me, NH CH (Me) C_〇 _{2 E t, NHCH (Me)} C 〇 _{2 P r, NHCH (Me)} C0 2 - iso- P r , NHCH (Me) C O2P n , NHCH (Me) C O2- cyclo -Pn, NHC_〇 _{2 Me, NH C O2E t,} n HC0 2 P r, NH C 0 2 - iso P r, NH C O2B u, NHC0 2 - cyclo- P r, NH C 0 2 - cyc 1 o- P n, NHC_〇 _{2 - iso- B u, NH C} 0 2 - sec- Bu, NH C 0 2 -tert—Bu, NHCO 2 CH 2 CH = CHCH ₃ , NHC0 ₂ CH ₂ CH2 CH ₂ , NHC 0 ₂ CH ₂ C≡ CH, NHC〇 ₂ Ph, NH C〇 ₂ CH ₂ Ph, NH C 0 _{2 CH 2 - (2 -M e -P} h), NH CO 2 C H2- (3 - Me- Ph), NH CO 2 CH2- (4 -M e -P h), NH C0 2 CH 2 - (4 -E t -P h), NH CO 2 C H2- (2-Me OP h), NH CO 2 CH2- (3-Me O-Ph), NH CO 2 C H2- (4-M e 0-P h), NH C 02 CH 2- (4-CI-Ph), NH CO 2C H2- (4-F-Ph), NH C 0 ₂ CH _2- (4-CF ₃ -Ph), NH CO 2C H2 -(2-F-Ph), NHCO2CH2- (3-F-Ph), NHCO2CH2- (3-CI-Ph), NHCO2CH2- (2-CI-Ph) _{), NHC0 2 CH 2 - (} 4- CF 3 0- Ph), NH S 0 2 Me, NHS_〇 _{2 E t, NH S 0 2} P r, NHS 0 2 - iso- P r, NHS 0 2 Bu, _{N HS0 2 CH 2 Ph, NH} S 0 2 CHC 1 2, NH SO 2C H2 C 1, NH S 02 CH 2 _{CH 2 C 1, NH S 0} 2 CH 2 CH 2 CH 2 C 1, NHS 0 2 CH 2 CF 3, NH S 02 Ph, N (SO 2E t) C0 2 E t, N (CH 2 〇_Me) S 〇 _{2 E t, N (CH2 CH} = CH 2) S 02E t, N (CH 2 C≡CH) S0 2 E t, N (Me) S 0 2 Me, N

(S 0 ₂ Me) ₂ , N (S 0 ₂ E t) ₂ , N (SO 2P r) ₂ , N (E t) SO 2E t, N (Me) SO 2E t, N (E t) SO 2E t, N (P r) S_〇 _{2 E t, N (COM e} ) S0 2 E t, N (C H2OM e) S 0 2 Me, N (CH 2O E t) S0 2 Me, N

(CH ₂ CH = CH2) S O2M e, N (CH ₂ C≡CH) S〇 ₂ Me, CONH SO ₂ Me, CONHS 0 ₂ Et, CONH S〇 ₂ CF ₃ , 1, 3—Dioxolan 1 2— Yl, 1,3-dioxane-2-yl, 4- [1- (ethoxycarbonyl) ethyloxy] phenyloxy, 4- [1- (methoxycarbonyl) ethyloxy] phenyloxy, N (Me) C0 ₂ Me, N (CH ₂ C3 CH) C〇 ₂ Me, N (Me) C〇Me, NHC〇Me, NHCOP r, N (CH ₂ C3 CH) COM e, N (CH ₂ CH = C H2) C0 ₂ Me, N (Me) CO 2 C H2- (4-M e-P h), N (CH ₂ C≡ CH) C0 ₂ Et, N (CH ₂ C≡N) C〇 ₂ Me , N (CO - tert -Bu) S_〇 ₂ Me, N (C_〇- tert-Bu) SO 2E t N (2 - Me O- _{Benzoiru) S0 2 Me, N (3-} M e 0- Benzoiru) S 〇 _{2 Me, N (4- M e} 0- _{Benzoiru) S 0 2 Me, N (} 2- M e 0- base _{Nzoiru) S 0 2 E t, N} (3- M e 0- Benzoiru) S 0 ₂ E t, N (4-Me 0-benzoyl) S 0 ₂ E t, N (4-Me- _{Nzoiru) S 0 2 Me, N (} 4- Me- _{Benzoiru) S0 2 E t, N (} 4 one CI- _{Benzoiru) S 0 2 Me, N (} 4- CI- Benzoiru) S_〇 ₂ E t, C O2- (N-CH 0) CH ₂ C0 ₂ Me, N (CHO) C H2C O 2E t, N (CH 0) C H2C 02P n, N (CH〇) CH

(Me) C_〇 _{2 Me, N (CHO) CH} (Me) C0 2 E t, N (COMe) CH 2 C0 2 Me, NHC0 CF 2 C 1, NHC0CF 3, C0NHMe, C0NMe 2, C0NE t 2, N (COMe) C H2 CO 2E t, N (COMe) C H2 CO 2P n, N (COMe) CH (Me) C0 ₂ Me, N (COMe) CH (Me) C 0 ₂ E t or N (CH2 C≡ N) S 0 ₂ Me, CH = C (CI) C0 ₂ Me, CH = C

(CI) C O2E t, 0 CH ₂ (4— CI— 2— (0 CH (Me) C0 ₂ Me)-phe ny l) or 〇 CH ₂ (4— Me— 2— (0 CH (Me) C0 ₂ Me)- phe ny l).

The R 4 H, F, C l , Me, E t, P r, iso- P r, Me O, E t O, P r O, CH2 C (Me) = CH 2 CH 2 CH = CH 2, CH ₂ C≡CH, 2,3-epoxy-1-methylpropyl or 2,3-epoxypropyl, preferably H or F. Incidentally, R4 is 2, when the 3-epoxy one 2-methylpropyl or _{CH 2 C (Me) = CH} 2, as R 3 include the substituent attached to Hue alkenyl group with an oxygen atom.

R 2 and R 3 may form a ring, in which case one R _{2 to} R 3 is one CH ₂ C (= 0) N (R 17) one,-SC (= 0) N (R 17 7) —or one NHCH ₂ C (= 0) N (R 17). Preferably, 1〇CHzC (= 0) N (R 17) 1 is used.

Examples of R 17 include the following substituents. Me, Et, Pr, iso—Pr, Bu, sec—Bu, iso—Bu, CH ₂ CH = CH ₂ , CH ₂ C≡CH, CH 2 C≡N, C H2C H2F, C H2CH 2C 1 , CH2 CH 2 C H2 F, CH ₂ 〇Me, 0 Me, 0E t, C H2O E t, C H2C H2 CH2C 1, CH 2 CH 2 CH 2 CH 2 F, CH ₂ CC 1 CH ₂ , CH ₂ CB _{r = CH 2, CH (Me} ) C≡CH, CH (Me) CH = CH 2 or CH (Me) C≡N.

The symbols in the text have the following meanings.

Me: CHs

E t: CH ₂ CH ₃

P r: CH ₂ C H2 CH ₃

isos-Pr: CH (CHs) 2

c y c l o -P r: CH (CH 2) 2

B u: CH ₂ CH ₂ CH 2 CH ₃

sec— Bu: CH (CHs) C 2 H 5 iso— Bu: CH ₂ CH (CH ₃ ) 2

tert -Bu: C (CH ₃ ) ₃

c y c l o-Bu: CH (C H 2) 3

P n: CH 2 CH ₂ CH 2 CH 2 CH a

cycl o-Pn: CH (CH ₂ ) ₄

is o-Pn: CH 2 CH 2 CH (CH ₃ ) 2

neo -P n; CH 2 C (CH ₃ ) 3

cyclo— He x: CH (CH ₂ ) ₅

tert—Pn: C (CH ₃ ) ₂ C ₂ H ₅

H ex: (CH 2) 5 CH ₃

H ep: (CH 2) 6 CH ₃

O ct: (CH ₂ ) 7 CH ₃

 Ph, Pheny l: C e H s

 4-C 1 -P h: 4 C I Phe ny l

 Some of the compounds of the present invention are used as herbicides for upland fields and non-cultivated lands. Eggplant slant. (Solanaceae) Weeds, Abui (Malvaceae) weeds typified by Abuti Ion theophrasti, American stag deer (Sida spinosa), etc., and Asagao (Ipomoea purpurea) ) And convolvulaceae (Convolvulaceae) weeds, such as convolvulaceae (Calvstegia spps.), Linbu (Amaranthus lividus), and aobu

(Amaranthus retrof lexus) and other weeds (Amaranthaceae) weeds; (Cirsium arvense) ノ stag beetle (Senecio vulgaris), Himejon

(Compositae) weeds such as (Erigeron annuus), cruciferae (Cruciferae) weeds, such as cruciferae (Cruciferae) weeds, such as crows m Blumei), Polygonaceae (Poly ^ s imm convolvulus i, etc.) gonaceae) Weeds, Poaceae (Portulaca oleracea), etc., as well as Posaceae (Portulacaceae) weeds, Shiroza (Chelia odium album), Kookasaza (Chenopodiu Ificifolium), and Okagi (Kochias coparia) (Chenop odiaceae) Weeds, Caryop hyllaceae weeds represented by Stellaria media, etc., Scrophulariaceae weeds represented by Veronica persica, etc., Commelina communis (Commelinaceae) weeds such as Laminariaceae (Lamium amplexicaule) and Laminaria purpureum (Lamium purpureum). Eubibiaceae (Euphorbiaceae) weed, Yaemugra (Galium aparine), Akane CRubia akane, etc. e) weeds, violets

Broad-leaved weeds such as Violaceae weeds represented by (Viola mandshurica) and leguminous weeds represented by leguminaceous weeds represented by Sesbania exaltata and Cassia obtusifolia , Wild sorghum (Sorgham bicolor), gifted wedge millet (Panicum dichotomif lorum), johnsongrass (Sorghum halepeiise), vine (Echinochloa crus-galli var.cs-galli), ) ^ Cultivated millet

(Echinochloa utilis), Meshishino, '(Digitaria adscendens), oats (Avena fatua), ohisino (Eleusine indica) ヽ Enokorogosa (Setaria viridis) It has high herbicidal activity at a low dose and various crop field weeds such as Cyperus rotundus and Cyperus esculentus (Cyperaceous weeds).

In addition, as a herbicide for paddy fields, in both soil treatment and foliage treatment under flooding, omomodaka typified by Heramodaka (Alisma canaliculatum), Omodaka (Sagittaria t rifolia), Perica (Sagittaria pygmaea), etc. family (Alisma taceae) weeds, evening Magayarri (Cvuerus difformis), Mizugayarri (Cyperus se rotiims)ゝho evening Louis (Scirpus .iuncoides j _s Kurokuwai (Kayarrigusa family represented by Eleocharis kuroguwai), etc. (Cyperaceae) weeds, Azena (Midernia £ ixida Scrothulariaceae weeds, such as Scrothulariaceae weeds, Potenderiaceae weeds, such as eel (Monoc horia vaginalis), and the piaceous weeds (Potamogetona e.), Such as potamogeton distinctus. , Lythraceae weeds represented by Rotala indica, etc., Echinochloa orvzicola (Echinochloa orvzicola), Echinochloa cr us-galli var. alii) Weeds and other various paddy weeds have low herbicide and high herbicidal activity. Furthermore, some of the compounds of the present invention have high safety against important crops such as rice, wheat, barley, sorghum, peanuts, corn, soybean, cotton, beet and the like.

The compound of the present invention can be synthesized, for example, by the methods shown in Schemes 1 to 15 (Z, A, Ra, Rc, Rf, Rg and Rl in Schemes 1 to 15: R ′ and R〃 each independently represent a C! —C ₄ alkyl group, H a 1 represents a halogen atom, and n represents an integer of 2 or 3.)

R1 R5

H ₂ N C0 ₂ R '

 = C, + SCN- R2

 Rf Rg

 1) base

R4 R3

 (II) (III) 2)

 (l: X— Y— N = N, A = N, Z = 0)

2)2(ORCRaCHa Hl-= (Scheme 1)

2) 2 (ORCRaCHa Hl- =

H)

(l: X-Y _{→ c (Ra) =} CH and / or CH = CRa,

 (A = N, Rg = H, Z = 0)

 (Scheme 3)

 (l: Z = 0, A = N, Rg CN) (l: Z = S, A = N, Rg ^ CN)

(Scheme 4) (l: XY— CH = CH, (l: X— Y— CH ₂ CH ₂ A = N, Z = 0) A = N, Z = 〇)

(Scheme 5)

H ₂ N tens CH ₂ " _n OH

^R3 J¾g

 R4

N S0 ₂ Me Rf

 (VI) HO CK (XVIII)

(I X- ^ Y— CH ₂ CH ₂ or CH ₂ CH ₂ CH ₂

 (A = N, Z = 0, n = 2 or 3)

(Scheme 6)

(l: X— Y— CH ₂ CH = CH, (IX— Y— CH = CHCH ₂

A = N, Z = 0) A = N, Z = 0)

(Scheme 7) (6 mer ^)

(. N = Z: I) (0 = Z: I)

 (8 mer)

 (0 = Z'N = V

 Ήθ = ΗΟ—person ^: l)

o PZSZ0 / L6d £ llDd zs / 86 ΟΛ \

o

()()〇 cco==

() () 〇 cco ==

,

 (l: X— Y— C (= 0) CH = N, A = N, Z = 0)

 (l: X Y- ^ C (= 0) NH,

 (A = N, Z = 0)

(Scheme 12)

(0 = Z'N = V

 'ο (ο =) ο—people ^ χ: ι)

 (ε I Ma ^^)

 .a ooio

 JO

z IOOO

LI

PZS £ 0 / L6d £ / ∑Dd / 86 OAV

2 CHCHO

 (l: X— Y → = CH,

 (A = CH, Z = 0, Rg = H)

(Scheme 15)

(Scheme 1)

 The aminocrotonate derivative (II) is reacted with the phenylisothiocyanate derivative (III) in the presence of a base in an inert solvent to give a 2-mercaptopyrimidine derivative (IV).

 Compound (II) is described in J. Org. Chem., 21, 1358-61 (1956); J. Heterocycl. Chem., 513 (1972); , Org. Kim, 22_ (8), 1603- 9 (1986); Japanese Patent Application Laid-Open No. 5-140060. Compound (III) was obtained from the corresponding aniline derivative by S and ler, SR, Karo, W. "Organic Functio nal Grou Preparations", Ad emic, New York, 1968, Vo. l.1, pp 312-31 Can be prepared according to the method described in 315.

By reacting compound (IV) with an alkylating agent such as dimethyl sulfate or methyl iodide (preferably Me, Et or the like as alkyl) in the presence of a base, for example, a 2-methylmercaptovirimidine derivative ( V) can be synthesized. The compound (V) can be derived into the 2-methanesulfonylbilimidine derivative (VI) using an oxidizing agent such as hydrogen peroxide, air, and metachloroperbenzoic acid. Compound (VI) is reacted with sodium azide (potassium azide or trimethylsilyl azide may be used) and the compound of the present invention (I: X to Y → N = N, A = N, Z = 0) Can be synthesized.

 The compound (VI) can be reacted with ammonia or ammonium acetate to lead to a 2-aminopyrimidine derivative (VII), or to react with hydrazine to lead to a 2-hydrazinopyrimidine derivative (VIII).

 However, by increasing the reaction conditions, the compound (VII), (VIII) or (I: XY → N = N, A = N, Z = (In the case of 0) can also be synthesized.

 (Scheme 2)

 The compound (VIII) was reacted with an orthoester derivative with reference to the method described in, for example, "Comprehensive Heterocyclic Chemistry" Vol. 5, Part 4 A, 890. Then, the compound of the present invention (I: X to Y → C (Ra) = N, A = N, Z = 0) can be synthesized.

 ^ O. (1) 235-237 (1992) and the like, referring to the halogenoacetaldehyde aldehyde dialkylase derivative (a chlorine atom and a chlorine atom as a halogen atom). And a compound of the present invention (I: X to Y → CH2 CRa, Α = Ν, Z = 0) or a compound of the present invention (I: X to Y → C (R a) = CH, A = N, Z = 0) can be synthesized.

 (Scheme 3)

It leads to guanidine derivative (XI) from sugar beetle (IX) and formyl aniline derivative (X). Further, the compound (XI) can be obtained by converting the keto acid ester derivative (XII) into a compound described in Helvetica Chimica Acta, Vol. 59, Fasc. 4 (19776) ppl 203-112, and the like. To obtain the compound of the present invention (I: X to Y → CH ₂ CH ₂ , A = N, R g = H, Z = 0). 1,2,4-triazole (XIII) having a methylmercapto group and imida 丄 The compound (XIV) can be reacted with the formyl aniline derivative (X) to synthesize the compounds (XIV) and (XVI). Subsequently, by reacting these with the β-ester derivative (XII), the compounds of the present invention (I: X to Y → N = CRa, A = N, R g = H, Z = 0) and The compound of the present invention (I: X to Y → C (Ra) = CHand / or CH = CRa, A = N, Rg = H, Z = 0) can be synthesized. In some cases, may also be subjected to the reaction as Me S group oxidizes, Me S_〇 ₂ group (XIII) and (XV). (Scheme 4)

Compounds (I: Z = 0, A = N, Rg ≠ CN) are converted to phosphorus pentasulfide (P ₂ S ₅ ) or oral lanthanide (Law sson's Reagent: 2, 4) One bis

The compound of the present invention (I: Z) is reacted with a thiocarbonylating agent such as (4-methoxyphenyl) — 1, 3-dithia-2,4-dithiophene-2,4-disulfide. = S, A = N, and R g ≠ CN) can be synthesized.

 (Scheme 5)

The compound (XVII) prepared from the compound (VI) and aziridine can be prepared by the method described in, for example, J. Org. Chem., Vol. 39, No. 24, 3508 (1974). The compound of the present invention (I: X to Y → CH ₂ CH ₂ , A = N, Z = 0) can be synthesized by reacting in the presence of sodium iodide or lithium iodide. Subsequently, the compound of the present invention (I: X to Y → CH = CH, A = N, Z) using an appropriate oxidizing agent such as air, NaOCl, DDQ, permanganate lithium or chloranil, etc. = 0).

 (Scheme 6)

YAKUGAKU ZAS SH I, 9_4. (1 2) Referring to the method described in ppl 503-1514 (1974), compound (VI) and the compound obtained from amino alcohol (XV III ) Is reacted with thionyl chloride or phosphorus oxychloride to give compound (XIX). This example DBU, pyridine, KOH, invention compounds are reacted with a base such as source Jiumume Tokisai de _{(I: X~Y → CH 2 CH} 2 orCH 2 CH 2 CH 2, A = N, Z = 0, n = 2 or 3) Wear. If a substituent such as methyl or phenyl is added to the carbon atom of the amino alcohol used in this reaction, a substituent corresponding to the methylene moiety of X to Y of the compound of the present invention can be introduced.

 (Scheme 7)

The compound (VII) is reacted with a halogeno-doped pyraldehyde dialkyl acetal (halogen is preferably chlorine or bromine), and then treated with a base to give a compound of the present invention (I: X to Y → CH ₂ CH = CH, A = It can be synthesized X to Y → CH two CHCH _2, a = N, if the Z = 0): N, in the case of Z = 0), or the present compound (I.

 (Scheme 8)

 The compound (V) is reacted with an aminoacetoaldehyde dialkyl acetal derivative with reference to, for example, J. Heterocyclic Chem., 26, 205-207 (11989), and to the 2-position 2,2— Compound (XX) can be synthesized by introducing a dialkoxyethylamino group. Further, the compound (XX) is subjected to a ring-closing reaction under acidic conditions, for example, in the presence of concentrated sulfuric acid, methanesulfonic acid, polyphosphoric acid, concentrated hydrochloric acid, paratoluenesulfonic acid, and the like, whereby the compound of the present invention (I: X to Y → CH CH, A = N, Z = 0) can be synthesized.

 (Scheme 9)

The compound (I: Z = 〇) is reacted with NH ₂ —R c after reacting with phosphorus oxychloride with reference to, for example, EP 1 682 62 and the like to give the compound of the present invention (I: Z = NR c Case) can be synthesized.

 (Scheme 10)

Compound (VII) is prepared by converting isocyanate R, NCO (R 'is preferably potassium, sodium or ammonium) or alkyl isocyanate R'NC0 (R' is methyl, ethyl, propyl, etc.). ) To produce a perylene derivative (XXI). Reacting the compound (XXI) with dimethylformamide dimethyl acetal to synthesize the compound of the present invention (I: XY → CH = NC (= 0), Α = Ν, Ζ = 0) Can be. The compound (XXI) is reacted with a phosgene derivative such as phosgene, phosgene dimer, triphosgene or a chloroformate to give a compound of the present invention (I: X to Y → C (= 〇) N (R,) C (= 0), Α = Ν, Ζ = 0) can be synthesized.

 The compound (VII) is reacted with a 3,3-dialkoxypropionic acid derivative, and the compound of the present invention (I: X to Y → C (= 0) CH = CH, A = N, Z = 0) is synthesized. Can be achieved.

 The compound (V I I) and chlorocarbon isocyanate were combined with, for example, Bu 11.

Jp n., 61, 22 17-22 19 (1988), etc., and reacted at once to obtain the compound of the present invention (I: X to Y → C (= 0) NHC (2 0), A = N, Z =）) can be synthesized. The compound (VII) can be reacted with acetic anhydride or acetyl chloride to lead to an acetoamide derivative (XXII). The compound (XXII) is reacted with DMF dimethyl acetal to synthesize the compound of the present invention (I: X to Y → CH = CHC (= 0), A = N, Z = 0).

(Scheme 11)

Compound (VII) a black hole acetate Kurorai de or is bromoacetate Kurorai de and reaction, the present compound: synthesizing _{(I X~Y CH 2 C (=} 0), A = N, if the Z = 0) be able to.

Reacting the compound (VII) with oxalyl chloride to synthesize the compound of the present invention (I: X to Y → C (= 0) C (= 0), where A = N, Z = 0) Can be. Compound (VII) and ethensulfonyl fluoride or chloroethyl sulfonyl chloride are referred to, for example, J. Or. Chem., Vol. 44, Νο.22, 3847-3858 (1979), etc. more reacting Te, compounds of the present invention: it is possible to synthesize (I X~Y CH ₂ CH ₂ S_〇 _2, a = N, if the Z = 0).

 (Scheme 1 2)

Compound (VIII) is converted to acetic acid chloride or bromoacetic acid chloride. By reacting, the compound of the present invention (I: X to Y → CH ₂ C (= 0) NH, A = N, Z = 0) can be synthesized.

 The compound (VIII) is reacted with glyoxylic acid (may be an ester form) or dimethyl acetal glyoxylate, and the compound of the present invention (I: X to Y → C (= 0) CH = N, A = N, Z = 0 ) Can be synthesized.

 The compound (VIII) is reacted with a phosgene derivative such as phosgene, phosgene dimer, triphosgene and the like, and the compound of the present invention (I: X to Y → C (= 0) NH, A = N, Z = 0) Can be synthesized.

 (Scheme 13)

 The compound of the present invention is obtained by reacting the compound (VI) with hydroxylamine to give the compound (XXIII) and subsequently reacting it with a phosgene derivative such as phosgene, phosgene dimer, triphosgene or a chloroformate.

(I: X ~ Y → C (= 0) 0, A = N, Z = 〇) can be synthesized. (Scheme 14)

 Compound (XXIV) and bromoacetaldehyde or chloroacetaldehyde can be used, for example, in J. Org. Chem., Vol. 42, No. 14, 24.

By reacting with reference to 48-2454 (1977), it is possible to synthesize the compound of the present invention (I: X to Y → CH = CH, A = CH, Z = 〇). Wear.

 Compound (XXIV) is reacted with a halogenating agent such as NBS, NCS, chlorine or bromine in the presence of BPO or AIBN to synthesize a halogenomethyl compound (XXV), which is subsequently reacted with formamide Then, the compound of the present invention (in the case of I: XY → CH = N, A = CH, Z = 0) can be synthesized by dehydration cyclization.

 Alternatively, after introducing an amino group into compound (XXV) to obtain compound (XXVI), the compound is subjected to formylation with formic acid with reference to, for example, USP 4,044, 015, etc., followed by dehydration with phosphorus oxychloride. Thus, the compound of the present invention (I: X to Y → CH = N, A = CH, Z = 〇) can be synthesized.

(Scheme 15) The compound (XXV II) is reacted with a /?-Keto acid ester derivative (XII) or a 2,2-ethoxyvinylhaloalkylketone (XXV III) to give a compound of the present invention (I: X to Y → N = CH, A = CH, Z = 0, and R g = H).

 The methylmercapto group and methanesulfonyl group of the compound (V) or (VI) in the scheme are used as leaving groups for the next reaction, but the compound containing a chlorine atom as the leaving group is used. A reaction may be performed.

 Hereinafter, synthesis examples of the compound of the present invention and intermediates are specifically described as examples, but the present invention is not limited thereto.

 (Example 1)

 Synthesis of 3- (4-chlorophenyl) -3,4-dihydro-2-methanesulfonyl 6-trifluoromethylpyrimidin-4-one

3- (4-chlorophenyl) -1,3,4-dihydro 2-methylthio-6-trifluoromethylbirimidine-1-one 1.0 g, 3-chloroperbenzoic acid 1.6 1 g, and a mixture of 2 ml of form 2 was stirred at room temperature for 12 hours. The mixture was washed twice with a saturated aqueous sodium hydrogen carbonate solution, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.1 g of the target substance as a white solid.

 (Example 2)

4- (4-chlorophenyl) 1-4,5-dihydro-7-trifluoromethylte tolazo [1,5-a] pyrimidin-5-one (Compound N 0.1) Synthesis

3- (4-chlorophenyl) 1-3,4-dihydro-2-methanesulfonyl-6-trifluoromethylbirimidine-14-one 1.1 g of acetonitril 20 m1, ether 2 The mixture was dissolved in a 0 ml mixture, and 0.24 g of sodium azide was added under ice cooling. The mixture was stirred at room temperature for 30 minutes, and 50 ml of saturated saline was added. After extraction with a ether, washing with water and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by a silica gel preparative thin layer plate (developing solvent: S-ethyl / hexane = 1.5 / 8.5) to obtain 0.7 g of the target product as a white solid.

'H-NMR (ppm) 6.67 (s, 1H), 7.14 (d, J = 8.5Hz, 2H), 7.53 (d, J = 8.5Hz, 2H) [CDC 1 _3] mp 8 1 - 8 3 ° C

 (Example 3)

 Synthesis of 3- (4-chlorophenyl) -1,3,4-dihydro-21-hydrazino-6-trifluoromethylbirimidin-4-one

3— （4一クロ口フエニル） 一 3， 4—ジヒ ドロー 2—メタンスルホ二ルー 6 — ト リフルォロメチルピリ ミジン一 4—オン 2. 0 gとテトラヒ ドロフラン 2 Omlの混合物の中にヒ ドラジン 1水和物 （ΝΗ₂ΝΗ₂ · H₂〇） 0. 5 gを加え た。 30分間室温で攪拌後、 飽和食塩水 30 m 1加え酢酸ェチルで抽出した。 抽出層を水洗後無水硫酸マグネシウムで乾燥した。 溶媒を減圧留去し、 乳白色 固体の目的物 1. 5 gを得た。

3- (4-chlorophenyl) -1,3,4-dihydro-2-methanesulfonyl 6-trifluoromethylpyrimidin-14-one Hydrazine in a mixture of 2.0 g and tetrahydrofuran 2 Oml 0.5 g of monohydrate (ΝΗ ₂ ΝΗ ₂ · H ₂ 〇) was added. After stirring at room temperature for 30 minutes, 30 ml of saturated saline was added, and the mixture was extracted with ethyl acetate. The extract layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.5 g of the target product as a milky white solid.

 (Example 4)

 8-(4-chlorophenyl) 1, 7,8-dihydro 5-trifluoromethyl-1,2,4-triazolo [4,3-a] pyrimidin-7-one (Compound No. 2 of the present invention) Synthesis of

3- (4-chlorophenyl) -1,3,4-dihydro-2, hydrazino-6-trifluoromethylpyrimidin-1,4-one 0.7 g, triethyl orthoformate 1.0 g, A mixture of 10 ml of acetic acid was heated at 120 ° C. for 1 hour. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel preparative thin layer plate (developing solvent: ethyl acetate / hexane = 4/6) to obtain 0.45 g of the desired product.

 -Title R (ppm) 6.75 (s, lH), 7.37 (d, J = 9Hz, 2H), 7.59 ((l, J = 9Hz, 2H), 8.37-8.48 (m, lH) CCD C 1)

mp 220-2 23 ° C

 (Example 5)

2-amino-3- (4-chloro-3-ethoxycarbonylphenyl) -1,3,4-dihydro-6-trifluoromethylpyrimidine-1

3- (4-chloro- mouth- 3-ethoxycarbonylphenyl) 1-3,4-dihydro-1-methanesulfonyl 6-trifluoromethylpyrimidin-14-one 1.0 g and dry THF 5 Oml Ammonia gas in the mixture

The solvent was distilled off under reduced pressure after blowing and drying over anhydrous magnesium sulfate. 0.7 g of the obtained white solid was used for the next reaction without purification.

 (Example 6)

 8- (4-chloro-1--3-methoxycarbonylphenyl) -17,8-dihydro 5 _trifluoromethylimidazo [1,2-a] bilimidin-7-one (Compound N of the present invention) Synthesis of 0.4)

CI Me, ci

 0 O

 Br, OMe

N C0 ₂ Et N, C0 ₂ Me

 AcONa

CF ₃ N NH K AcOH CF to N N

 w

2-amino-3- (4-chloro-3-ethoxycarbonylphenyl) 13,4 dihydro-6-trifluoromethylpyrimidine-14one 0.7 g, bromoacetaldehyde dimethyl acetal A mixture of 0.65 g, sodium sulfate, 0.24 g, and acetic acid, 10 ml, was heated to reflux for 4 hours. The solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The extract layer is washed with water and dried over anhydrous magnesium sulfate. Distilled off. The residue was purified by an alumina preparative thin layer plate (developing solvent: ethyl acetate / hexane = 25/75) to obtain 0.15 g of the desired product as a solid.

'H-NMRippm) 3.92 (s, 3H), 6.72 (s, 1H), 7.15 (d, J = 1.8 Hz, 1H), 7.31 (d, J = 1.8 Hz, 1H) _; 7.54-7.68 (m , 2H), 7.97-8.04 (m, lH) [CD C 1 _3]

mp l 8 0-1 8 3 ° C

 (Example 7)

 8- (4-chloro-1--2-fluoro-5-nitrophenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2, a] pyrimidin-7-one (the present invention) Synthesis of Compound N 0.7)

8- (4-chloro-2-1-fluorophenyl) -Ί, 8-dihydro-5-trifluoromethylimidazo [1,2-a] pyrimidin-7-one 0.8 g of concentrated nitric acid

(60%, d = 1.38) 1 ml and concentrated sulfuric acid 10 ml were added under ice cooling to a mixture. The mixture was reacted at 0 ° C for 30 minutes and poured into 150 ml of ice water. The mixture was extracted with ether, and the extract layer was washed with water, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.65 g of the desired product as a solid.

'H-NMR (ppm) 6.64 (s, 1H), 7.08 (d, J = 1.2 Hz, IH), 7.24 (d, J = 1.2 Hz, 1H), 7.49 (d, J = 9 Hz, 1H ), 9.16 (d, J = 6Hz, lH) [CD C 1 _3]

m 1 7 1-1 7 3 ° C

 (Example 8)

8- (5-amino-1-4-chloro-2--2-fluorophenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2-a] pyrimidin-7-one Synthesis of clear compound N 0.8)

8- (4-chloro-1--2-fluoro-5-nitrophenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2, a] pyrimidin-7-one 0.6 g 0.5 g of iron powder was added to a mixture of 5 ml of ethyl acetate, 2 ml of acetic acid and 10 ml of water, and the mixture was refluxed for 3 hours. The mixture was filtered through celite and the solid was washed with hot ethyl acetate. The organic layer was separated from the filtrate and the washing solution, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.52 g of the desired product as a solid.

'H-NMR (ppiii) 3.98-4.23 (br, s, 2H) ₎ 6.60 (s, lH), 6.68 (d, J = 6Hz, lH) ₎ 7.04-7.28 (m, 3H) (CD C 13)

mp l 84-1 86 ° C

 (Example 9)

 8- (4-chloro-5-ethylsulfonylamino-2-fluorophenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2, a] pyrimidin — 7-one Synthesis of (Inventive Compound No. 6)

8-(5-Amino-4 monochloro-2-fluorophenyl) -17,8-dihydro5-trifluoromethylimidazo [1,2, a] pyrimidin-7-one 0. In a mixture of 49 g and 15 ml of methylene chloride, 0.22 g of ethanesulfonyl chloride and then 0.17 g of pyridine were added dropwise. The mixture was stirred at room temperature for 3 days, added with 50 ml of chloroform, washed with water, diluted hydrochloric acid and water in that order, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with an alumina preparative thin-layer plate (developing solvent: ethyl acetate / hexane = 1/1) to obtain 0.08 g of the desired product as a solid.

'H-NMR (ppm) 1.35 (t, J = 7 Hz, 3H), 3.10 (q, J = 7 Hz, 2H), 6.58 (s, lH), 7.03-7.42 (m, 4H) _: 7.71 (d, J = 6Hz, lH) CCD C 1 3 ]

mp 22 6-229 ° C

 (Example 10)

 8- (4-chloro-1-3-ethoxycarbonylphenyl) -17,8-dihydro-2-methyl-5-trifluoromethylimidazo [1,2-a] birimidine-1 7-on (book Synthesis of Invention Compound No. 13)

2-Amino 3- (4-chloro-mouth _3-Ethoxycarbonylphenyl) -3,4 Dihidro 6-Trifluoromethylbirimidine 4-one 0.5 g, Promorecetone dimethylase 0 1 g A mixture of 0.6 g and 10 ml of DMF was heated and stirred at 130 ° C. for 5 hours. The solvent was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with an alumina preparative thin layer plate (developing solvent: ethyl acetate / hexane = 3/7) to obtain 11 g of the desired product.

lH-NMR (ppm) 1.38 (t, J = 7Hz, 3H), 2.22 (s, 3H), 4.39 (q, J = 7Hz, 2H), 6.62 (s, 1H), 7.00 (s, lH), 7.48 ((ld, J = 8,3Hz, lH), 7.64 ((i (i, J = 8,0.5Hz, lH), 7.95-7.96 (m, lH) CCD C 1 a)

mp l 73-1 75 ° C

 (Example 11)

 8-(4 1-mouth 5-ethylsulfonylamino-2-fluorophenyl)-7,8-dihydro-1-trifluoromethylimidazo [1, 2-a] birimidine-7-thione ( Synthesis of Compound of the Invention N 0.20)

8- (4-chloro-1-5-ethylsulfonylamino-2-fluorophenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2-a] pyrimidin — 7-one 0 A mixture of 0.6 g, 0.5 g of diphosphorus pentasulfide, and 30 ml of toluene was heated to reflux for 3 hours. The solid was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate) to obtain 0.5 g of the desired product as yellow crystals.

'H-NMRCppm) 1.31 (t, J = 8Hz, 3H), 3.08 (q, J = 8Hz, 2H), 7.14 (s, lH), 7.25-7.70 (m, 4H) _: 9.33-9.42 (br s, lH) [CD C 1 ₃ + DMSO- d _e]

m p> 2 20 ° C (decomposition)

(Example 12)

8- (4-chloro-1--2-fluoro-5-phenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2-a] pyrimidin-7-one (Compound No. Synthesis of 2 5) CF, Ν 'N

8-(4-Chloro-2-fluoro-5-hydroxyphenyl) -17,8-dihydroxy-5-trifluoromethylimidazo [1,2, a] pyrimidin-1 7-one 43g, propargylrube A mixture of 2.3 g of mede, 2.1 g of potassium carbonate and 10 Oml of acetonitrile was heated to reflux for 2 hours. The solvent was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from diisopropyl ether to obtain 4.2 g of the desired product as milky white crystals.

'H-NMR (ppm) 2.46-2.55 (m, IH), 4.67-4.74 (m, 2H), 6.71 (s, 1H), 7.00-7.22 (m, 3H), 7.30 (d, J = 9 Hz, lH ) [CDC 1 _3]

mp l 54-1 56 ° C

(Example 13)

 8- (4-cyano 2-fluoro-5-phenyl) -7,8-dihydro 5-tritrifluoromethylimidazo [12-a] pyrimidin-1 7-one (Compound No. 34 of the present invention) Synthesis

8— （ 4一シァノ一 2—フルオロー 5—ヒ ドロキシフエニル） 一 7 , 8—ジヒ ドロ一 5 _ ト リフルォロメチルイ ミダゾ 〔 1， 2— a〕 ビリ ミジン一 7—オン 0

8- (4-cyano-2-fluoro-5-hydroxyphenyl) -17,8-dihydro-5_trifluoromethylimidazo [1,2-a] birimidine-1 7-one 0

A mixture of 23 g, 0.16 g of propargylbutene, 0.14 g of potassium carbonate and 15 ml of acetonitrile was refluxed under heating for 2 hours. The solvent was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from diisopropyl ether.

17 g were obtained as milky white crystals.

'Η-thigh (ppm) 2.52-2.60 (m, lH), 4.75-4.83 (m, 2H), 6.65 (s, lH), 7.05-7.27 (m, 3H), 7.50 (d, J = 9Hz, lH ) [CDC 1 _3]

mp l 30-1 32 ° C

 (Example 14)

 Synthesis of 3- (4-promo 2-fluorophenyl) -1,3,4-dihydro-2-((2,2-diethoxyshethyl) amino) -1 6-trifluoromethylpyrimidine-14-one

3-(4-butane-2-fluorophenyl) -1,3,4-dihydro-2-methylthio-6-trifluoromethylpyrimidin-1 4-one 21.5 g, aminoacetoaldehyde 15 g of tilacetal was stirred at 130 ° C. for 3 hours. Excess aminoacetoaldehyde decyl acetal was distilled off under reduced pressure, and the residue was used for the next reaction as it was. (Example 15)

 Synthesis of 8- (4-bromo-1-fluorophenyl) -17,8-dihydr-5-trifluoromethylimidazo [1,2-a] pyrimidin-7-one (Compound N 0.69)

3- (4-1-Bromo-2-fluorophenyl) -1,3-dihydro-1-2-((2,2-diethoxyshetyl) amino) -16-trifluorometylpyrimidine-1-one synthesized in Example 14 Was dissolved in 10 Oml of concentrated sulfuric acid under ice-cooling and stirred at room temperature for 4 hours. The reaction solution was poured into 500 ml of ice water, and neutralized with a sodium hydroxide aqueous solution under ice cooling. The mixture was extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the obtained solid was washed with isopropyl ether to obtain 17.5 g of the desired product as a pale yellow solid.

lH-NMR (ppm) 6.83 ( s, lH), 7.24-7.75 (m, 5H) [CD C 1 _3]

m 1 69-1 71 ° C

(Example 16)

8- (4-Bromo-2-fluoro-5-ditrophenyl) -1-7,8-dihydro-5-trifluoromethylimidazo I: 1,2-a] Pyrimidin-1-7-one F CH ₂ SO '4

8-(4-Bromo-2-fluorophenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2, a] pyrimidin-17-one Dissolve 12 g in 50 ml of concentrated sulfuric acid Then, 5.0 g of nitric acid (60% d = 1.38) was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into ice water, and the obtained solid was collected by filtration. The solid was washed with water and dried to obtain 12.5 g of the desired product.

 (Example 17)

 8- (5-amino-4-bromo-1-fluorophenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2-a] pyrimidin-7-one (Compound N of the present invention) 0.7.70)

8- (4-Bromo-2-fluoro-5-nitrophenyl) -7,8-dihydro-5-trifluoromethylimidazo [1,2-a] pyrimidin-7-one synthesized in Example 16 12.5 g and 8.0 g of iron powder were added to a mixed solution of 100 ml of water, 50 ml of ethyl acetate, and 50 ml of acetic acid, and heated under reflux for 3 hours. Reaction solution The celite was washed with hot ethyl acetate. The filtrate and the washing solution were mixed, washed with water, saturated sodium hydrogen carbonate and water in that order, and dried over anhydrous magnesium sulfate. After removing the vicinity of the origin with an alumina short column, the solvent was distilled off under reduced pressure. The obtained solid was recrystallized from isopropropyl alcohol / isobrovir ether = 1/9 to obtain 9.3 g of the desired product.

 'H-NMR (ppm) 4.07-4.35 (br s, 2H), 6.80 (s, lH), 6.82-6.96 (m, lH), 7.23-7.61 (m, 3H)

(C D C 1)

mp 2 0 9-2 1 0 ° C

 (Example 18)

 8- (5-Amino-1-4-cyano 2-fluorophenyl) -17,8-dihydro 5-tritrifluoromethylimidazo [1,2-a] pyrimidin-7-one (Compound N 0 of the present invention) . 7 1) Synthesis

8— (5-Amino-4-bromo-1-fluorophenyl) —Ί, 8-dihydro-5-trifluoromethylimidazo [1,2—a] pyrimidin-7-one 3.7 g, A mixture of 1.lg of copper (I) cyanide and 30 ml of dimethyl sulfoxide was heated and stirred at 170 ° C for 5 hours in a nitrogen atmosphere. After cooling to room temperature, 1.0 g of iron chloride and 2 ml of 6N hydrochloric acid were added, and the mixture was stirred at room temperature for 15 minutes. The reaction solution was poured into 200 ml of water, extracted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained solid was washed with ether to obtain 2.2 g of the desired product. 'H-NM (ppni) 5.30-5.43 (br s, 2H), 6.65 (s, lH), 6.73-7.47 (m, 4H) [CDC 1 mp 2 0 1 -2 0 3 ° C (Example 19)

 8- (4-promo 2-fluoro-5-methylsulfonylaminophenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2, a] pyrimidine-17one (compound of the present invention) No. 49)

8- (5-Amino-1-bromo-2-fluorophenyl) -17,8-dihydro-5-Trifluoromethylimidazo [1,2-a] Birimidin-1 7-one 5.0 g, methane A mixture of 1.21 g of sulfonyl chloride, 2.02 g of pyridine, and 30 ml of methylene chloride was stirred at room temperature for 5 days. The reaction solution was poured into water and extracted with ethyl acetate. The extract layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The remaining solid was washed with ^{_{ether, 4. 8 g c 1 H-}} NMR of the desired product as a white solid (ppm) 3.04 (s, 3H ), 6.71 (s, lH), 7.10 (s, lH) , 7.26-7.38 (m, lH), 7.56 ((i) J = 6Hz, lH)) 7.68 (d, J = 4Hz, lH), 9.04-9.13 (br s, lH) [CDC 1 ₃ + DMS 0- d

mp 238-240 ° C

(Example 20)

8- (4-Cyano-2-fluoro-5-nilaminophenyl) 1 7 8-Dihydro 5-tritrifluoromethylimi [1,2, a] pyrimidin-1 7-one (Compound N of the present invention) o. 5 1)

8- (4-Bromo-1-fluoro-5-methylsulfonylaminophenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2-a] birimidine — 7-one 3.0 g, 0.86 g of copper (I) cyanide, and 30 ml of dimethyl sulfoxide were heated at 160 ° C. for 7 hours under a nitrogen atmosphere. After cooling to room temperature, 0.8 g of iron chloride (11) and 1.5 ml of 6N hydrochloric acid were added, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was poured into ice water, and the obtained solid was filtered and washed with ethyl acetate. The solid was dissolved in acetonitril and the vicinity of the origin was removed with a silica gel short column. The eluate was concentrated to the extent that crystals did not precipitate, 5.0 g of alumina for column chromatography was added, and the mixture was stirred for 15 minutes. The alumina was separated by filtration, washed with a small amount of acetonitrile, and eluted with 30 ml of an acetonitrile solution containing 5% of triethylamine and water. The eluate was distilled off under reduced pressure, and 10 ml of ethyl acetate, 20 ml of water, and 10 drops of 6N hydrochloric acid were added to the residue. After vigorous stirring, the obtained solid was collected by filtration. The solid was washed with water and ethyl acetate, and dried to obtain 0.6 g of the desired product as a white solid.

^{1 H-NMR (ppm) 3.06} (s, 3H)) 6.67 (s, lH)) 7.01-7.08 (m, lH), 7.18-7.34 (i, lH), 7.60 ((l, J = 6Hz, lH) , 7.73 (d, J = 4Hz , lH), 10.08-10.20 (br s, lH) [CD C 1 _3]

m p> 300 ° C (decomposition)

 (Example 21)

8— (4-chloro-1--5- (2-chloro-1-ethoxycarbonyl) ethyl-1-fluorophenyl) -1,7,8-dihydro 5-tritrifluoromethylimidazo [1,2—a Synthesis of Pyrimidin-7-one (Compound No. 54 of the Present Invention)

8- (5-Amino-4-1-chloro-2-fluorophenyl) -17,8-dihydro-5-Trifluoromethylimidazo [1,2-a] pyrimidin-1-7-one 1.5 g, chloride To a mixture of 0.06 g of copper (I) and 30 ml of acetone, 1.13 g of concentrated hydrochloric acid and 5.0 g of ethyl acrylate were added under ice cooling. 0.38 g of sodium nitrite was dissolved in water, added slowly under ice-cooling, and stirred at room temperature for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract layer was washed with diluted hydrochloric acid and then with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by a silica gel preparative thin layer plate (developing solvent: ethyl acetate / hexane = 3/7) to obtain 0.5 g of the desired product as a pale yellow oil.

^{1 H-NMR (ppm) 1.24} (t, J = 6Hz, 3H), 3.22-3.48 (m, 2H), 4.18 (q, J = 6Hz, 2H), 4.51 (t, J = 7H z, lH), 6.60 (s, lH), 6.98-7.39 (m, 4H) [CDC 1 _3]

no ²⁰ - ⁵ 1. 53 37

 (Example 22)

2-chloro-1- (4-fluoro-2-fluorophenyl) -7,8-dihydr-5-trifluoromethylimidazo [1,2-a] pyrimidin-7-one (The present invention Synthesis of compound N 0.55)

8— (4—Black D—2—Fluorophenyl) -17,8—Dihydro-5—Trifluoromethylimidazo [1,2—a] Pyrimidin-1 7-one 1.0 g, N—Black Mouth amber A mixture of 0.4 g of the acid imide and 30 ml of acetonitril was heated under reflux for 3 hours. The solvent was distilled off under reduced pressure, and the residue was purified by a silica gel preparative thin layer plate (developing solvent: ethyl acetate / hexane = 2/8) to obtain 0.3 g of the desired product.

 -NMR (ppm) 6.77 (s, lH), 6.97 (s, lH), 7.18-7.42 (m, 3H) (C D C 1

mp l 57-1 59 ° C

 (Example 23)

 8- (2-Fluoro-4-— ((4-Methyl-2- (methoxycarbonyl-1-ethyloxy) phenyl) methoxy) phenyl) 1,7,8-Dihydro-5-trifluoromethylimidazo [1, 2—a] Synthesis of pyrimidin-7-one (the present compound N 0 6 2)

0, no C0 ₂ Me ₀

K ₂ C0 ₃

C0 ₂ Me DMF F ₃ C 8— (2-Fluoro-1-4-hydroxyphenyl) -17,8-dihydro-5-trifluoromethylimidazo [1,2-a] Birimidin-1 7-one 200 mg dissolved in 6 ml of DMF Then, 106 mg of potassium carbonate and 150 mg of methyl 2- (2- (clomethyl) -15-f "methylphenoxy) propanoate were added thereto, followed by stirring at 75 ° C. for 2 hours. Water was added to the mixture, and the mixture was extracted with getyl ether.The organic layer was dried over magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was separated with a silica gel preparative thin layer plate (developing solvent: ethyl acetate / Hexane = 2/3) to give 170 mg of the desired product.

^{1 H-NMR (ppm) 1.63} (d, J = 7Hz, 3H), 2.32 (s, 3H), 3.74 (s, 3H), 4.85 (q, J = 7Hz, lH), 5.20 (s, 2H), 6.51-7.50 (m, 9H) [CD C 1 _3]

n _D ²¹ ' ¹ 1.39 1 2

 Tables 1 and 2 show the structural formulas and physical properties of the compounds of the present invention synthesized according to the above Examples, including the above Examples.

[table 1]

化合物 No. Rf X〜Y Z Rl R2 R3 R4

Compound No.Rf X ~ YZ Rl R2 R3 R4

1 CFs N = N 0 H CI H H

2 CF ₃ CH = N 0 H CI HH

3 CF CH = CH 0 H CI H H

4 CF ₃ CH = CH 0 H CI COzMe H

5 CF ₃ CH = CH 0 F CI HH

6 CF ₃ CH = CH 0 F CI NHS0 ₂ Et H

7 CF ₃ CH = CH 0 F CI N0 ₂ H

9 CF ₃ CH = CH 0 F CI NHS0 ₂ Me H

10 CFs CH = CH 0 F CI NHC0 ₂ Me H

11 CFs CH = CH 0 H CI C0 ₂ Et H

12 CFs CH = CH 0 F -0CH ₂ C0N (CH ₂ C≡CH)-H

13 CF ₃ CH = CMe 0 H CI C0 ₂ Et H

14 CFs CH = CH 0 F CI N (CHO) CH ₂ C0 ₂ Me H

15 CF ₃ CH = CH 0 F CIN (CHO) CH (Me) C0 ₂ Et H

16 CFa CH = CH 0 F CI NHS0 ₂ Pr H

17 CF ₃ CH = CH 0 F CI NHSO2BU H

18 CFs CH = CH 0 F CI 0-cyclo-Pn H

19 CF ₃ CH = CH 0 H CI H

20 CFa CH = CH s F CI NHSC Et H

21 CFa CH = CH 0 F CI OMe H

22 CFs CH = CH 0 F CI OH H

23 CFs CH = CH 0 F CI 0CH ₂ C0 ₂ Et H H ^s H ³ D ^z 0SHN J8 i 0 HD = HO Hd 9

HN≡3 ² H00 N≡0 ί 0 Η3 = Η0 Hd S

HU (i ^z 00 ^z H00 N≡0 ί 0 H3 = HD Hd

 H, jg J 0 ΗΟ = ΗΟ Hd ε

H H0≡0 ^z H00 J 0 HD = HO

H ^Ε Η0 ^ε 000 N≡0 J 0 HD = HO Hd

 H N≡D J 0 ΗΟ = ΗΟ Hd 6S

HN≡0 0 HO = HD ^E i3 8C

I 0 HD≡0 ^J HD0 10 ί 0 ΗΟ = ΗΟ Hd LZ

H N≡D I 0 Η3 = Η0 HO 9ε

H 9N0 N≡3 I 0 Η3 = Η0 HO

H HD≡0 ^z H00 N = 0 J 0 ΗΟ = ΗΟ HO K

H TO ί 0 ΗΟ = ΗΟ ^E J0 εε

H ID ί 0 ΗΟ = ΗΟ H zz

H 3 (9W) H:) 0 10 ί 0 HO = HD H \ z

H 8W ³ 0S (T ^ o ^ AXd) N TO I 0 Η0 = Η3 Hd οε

^SJ3 62H 9 0S (

^S J3 62

H (ozusq οΐ ω- 13 ί 0 ΗΟ = ΗΟ Hd

 I

H Ϊ3 ^Ζ 00 (9Ν) Η30 TO I 0 HJ-HO ^E iJ

H -id-osT-0 TO ί 0 ΗΟ = ΗΟ ^E J0

H H0≡0 ³ HD0 Id ί 0 HD = HD Hd

H ^ a ^z 0S (T ^ oi ^ d) N TO i 0 HD = HO Hd nn sa ΖΈ.

f9

PZS £ 0 / L6d £ llDd / 86 OAV Compound No.Rf XYZ Rl R2 R3 R4

47 CF3 CH = CH 0 F Br 0-iso-Pr H

48 CFs CH = CH 0 F Br 0-cyclo-Pn H

49 CFs CH = CH 0 F Br NHS0 ₂ Me H

50 CFs CH = CH 0 FC≡N NHS0 ₂ Et H

51 CF ₃ CH = CH 0 FC≡N NHS0 ₂ Me H

52 CFs CH = CH 0 CI CI OMe H

53 CFs CH = N 0 F Br OMe H

54 CF ₃ CH = CH 0 F CI CH ₂ CH (C1) C0 ₂ C2H5 H

55 CF ₃ CH = CC1 0 F CI HH

56 CF ₃ CH = CBr 0 F CI Me H

57 CFs CH = CH 0 CI CI 0CH ₂ C≡CH H

58 CFs CH = CH 0 CI CI 0-iso-Pr H

59 CF ₃ CH = CH 0 CI CI Ocyclo-Pn H

60 CFs CH = CH 0 FC≡N NHCOCFa H

 62 CFs CH = CH 0 F Q 2 H H

63 CF ₃ CH = CH 0 FQ 3 HH

64 CFs CH = CH 0 F CI NHCHzC = CH H

65 CFs CH = CH 0 F CI N (S02Me) CH2C = CH H

66 CF ₃ CH = CH 0 FQ 4 HH

67 CF ₃ CH = CH 0 F Br Q 2 H

68 CF ₃ CH = CH 0 F Br 0CH ₂ CH = CH ₂ H

69 CFs CH = CH 0 F Br HH vr>

 1 ϋ a W IN 0.ill Λ Y V 7 P

 I 1 DO

 Λ Λ¾

70 CFs CH = CH 0 F Br NH ₂ H

71 CF ₃ CH = CH 0 FC≡N NH ₂ H

73 CF ₃ CH = CH 0 FC≡CSiMe ₃ HH where Q 1 Q 4 represents the following substituents,

Q3

Q4

[Table 1 2] Compound No physical properties

1 mp 8 1-8 3 ° C 2 mp 2 2 0 ~ 2 2 3 ° C 3 mp 2 1 3-2 16 ° C 4 mp 1 8 0-1 8 3 ° C 5 mp 1 6 5-1 6 8 ° C 6 mp 2 2 6-2 2 9 ° C 7 mp 1 7 1 1 1 7 3 ° C 8 mp 1 8 4-1 8 6 ° C 9 mp 2 4 0-2 4 3 ° C

1 0 mp 1 8 1 1 1 8 3 ° C 1 1 mp 1 2 6 1 1 2 8 ° C 1 2 mp 2 3 9 1 2 4 1 ° C 1 3 mp 1 7 3-1 7 5 ° C 1 4 mp 7 2 1 7 4 ° C 1 5 mp 5 3 1 5 5 "C 1 6 mp 2 0 5-2 0 8 ° C 1 7 mp 1 8 0-1 8 3 ° C 1 8 mp 1 5 7-1 5 9 ° C 1 9 mp 1 3 3-1 3 5 ° C 2 0 mp> 2 2 0 ° C (decomposition) 2 1 mp 1 4 5-1 4 7 ° C 2 2 mp 2 5 5-2 5 7 ° C 2 3 mp 1 1 0— 1 1 2 ° C Compound No physical properties

2 4 m p 1 7 5-1 7 8 ° C

2 5 m p 1 5 4-1 56 ° C

2 6 m p 1 4 4 1 1 4 6 ° C

2 7 ri D ^{2 5} 1 .5 2 4 8

2 8 mp 72-75. C

2 9 m p 9 0 1 9 3 ° C

3 0 mp 2 0 9-2 1 2 ° C 3 1 mp 1 2 1-1 2 3 ° C 3 2 mp 1 2 0-1 2 2 ° C 3 3 mp 1 2 7 1 1 2 9 ° C 3 4 mp 1 3 0-1 3 2 ° C 3 5 mp 2 0 0-2 0 2 ° C 3 6 mp 1 6 3-1 6 5 ° C 3 7 n D ^{2 7} 1 .5 2 8 0 3 8 mp 1 4 3-1 4 5 ° C

3 9 m p 1 4 4-1 46 ° C

4 0 mp 7 9 1 8 1 ° C 4 1 mp 1 7 0-1 7 2 ° C 4 2 mp 1 2 7-1 2 9 ° C 4 3 mp 1 4 2-1 4 3 ° C 4 4 mp 1 3 2—1 3 4 ° C 4 5 mp 2 1 8-2 2 0 ° C 4 6 mp 2 1 0-2 1 2 ° C Compound No physical properties

47 mp 101-1 03 ° C 48 mp 1 72-1 74 ° C

49 mp 2 38—240 ° C

50 mp 2 35-238 ° C 51 mp> 300 ° C (decomposed) 52 mp 72-75 ° C 53 mp 2 50-2 52 ° C 54 n _D ² . ^{. 5 1. 5337 5 5 mp 1} 57- 1 59 ° C 56 mp 1 3 5- 1 37 ° C 57 n D 20 - 6 1. 5624 58 m 1 39 - 1 4 1 ° C

59 mp 1 33— 1 3 5 ° C

60 mp 2 08- 2 1 0 ° C 6 1 n D 21 - 1 1. 5074

63 mp 1 1 0—1 13 ° C 64 mp 202-205 ° C 65 mp 89-91 ° C 66 mp 1 42—1 44 ° C 67 mp 57-60 ° C 68 mp 60-63 ° C 69 mp 1 69-1 7 1 ° C Compound N ο Physical Properties

70 mp 209 2 1 0 ° C

 7 1 mp 20 1 203 ° C

 72 mp 1 1 8 1 20 ° C

73 mp 1 170 1 72 ° C Tables 3 and 4 show the compounds of the present invention synthesized according to the above schemes or examples, including the compounds synthesized in the above examples, but the present invention is limited by these. It is not something to be done.

[ε-¾]

PZSZ0 / L6d £ / 13d Ϊ9 / 86 OAV

CH,

mzs £ 0 /, 6ev zs / 86 OAV.l: £-

 19

PZS £ 0 / L6dr / lDd / 86 OAV

89

ZS £ 0 / L6dr / ∑Dd ZSPPVS6 OAV

PZS £ 0 / L6d £ / lDd

PZS £ 0 / L6d £ / lDd

PZSZ0 / L6dT / lDd

^ rS0 / .6Jf / I3d:

PZS £ 0 / L6dT / lDd / 86 OAV

PZS £ 0 / L6d £ / lOd L

/ 86 OAV

ZS£0/L6i£/lDd 9 OAV

ZS £ 0 / L6i £ / lDd 9 OAV

8

fZS € 0 / L6df / XDJ / 86 OAV

or oil

R 3

H, CI, F, B r , I, CH_〇, C O2H, CONH2, S O2C 1, _{C_〇_Me, SH, OH, NH 2,} NO2, CN, P henl, Me, E t, P r, iso -Pr, Bu, sec—Bu, iso—Bu, tert—Bu, Pn, neo—Pn, tert—Pn, cyclo—Pr, cyclo—Bu, eye 1 o—Pn, cyclo -H ex, CH ₂ CH2 CH ₂ , CH (Me) CH = CH ₂₎ CH ₂ C≡ CH, CH (Me) C≡ CH,

0—Me, 0—Et, O-iso-Pr, 0—Pr, 0—Bu, 〇—sec—Bu, 0—iso—Bu, 0—eye 1 o—Pn, 0 — Cyclo— P r, 0— cyclo -H ex, On eo -P n, 0- tert -P n, 0-P n, 〇 一 H ex, 0— H ep, 0— Oct, 0 CH2 CH = CH ₂ , 0 CH (Me) CH2 CHz, 〇 C (Me) ₂ CH = CH ₂₎ O CH ₂ C≡ CH, O CH (Me) C≡ CH, 0 C (Me) ₂ C≡ CH, 0 CH ₂ CH = C (CI) H, 0 CH2C (CI) = CH 2, 0 CH2C F ₃ , O CH ₂ CH ₂ OMe, 〇 CH ₂ CH ₂ OE t, 〇 CH ₂ OMe, 0 C H2O E t, 0 CH ₂ — cyc 1 o -Pr, 0 CH2CN, 0 COM e, 〇C0Et, 0 C0Pr, OCO-iso-Pr, 0 CH2C (Me) = CH2, 0—iso— P n,

S—Me, S—Et, S-iso-Pr, S-Pr, S-Bu, S—sec—Bu, S-iso-Bu, S—cyclo—Pn, S—cyclo — P r, S— cyclo -H ex, S -neo -P n, S-tert -P n, S-P n, S -H ex, S-Hep, S— Oct, S CHzCH = CH ^ , SCH (Me) CH = CH ₂ , SC (Me) ₂ CH = CH2, S CH ₂ C 3 CH, S CH (M e) C≡ CH, SC (Me) zC≡ CH, S CH ₂ CH = C (CI) H, S CH2C (CI) = CH 2, SCH ₂ CF 3, S CH ₂ CH ₂ OMe, S CH2C H ₂ OE t, o 1

R 3

S CH2OM e, S CH2O E t, S CH _2- cyclo—P r, S CH2CN, NH— Me, NH-E t, NH-iso-P r, NH-P r, NH-Bu,

NH—sec—Bu, NH-iso-Bu, NH-cyclo-Pn, NH-cyclo—Pr, NH-cyclo-Hex, NH-neo-Pn, NH—tert-Pn, NH - P n, NH- H ex , NH-H ep, NH- O ct, NH CH 2 CH = CH 2, NH CH (Me) CH = CH2, NH C (Me) 2 CH = C H2, NH CH _{2 C≡ CH, NH CH (Me} ) C≡ CH, NH C (Me) 2 C≡ CH, NH CH 2 CH = C (CI) H, NH CH 2 C (CI) = CH2, NHCH 2 CF 3, NH CH ₂ CH ₂ OMe, NH CH2CH2O E t, NH CH ₂ 〇Me, NH C H2O E t, NH CH ₂ — cyclo—P r, NH CH2CN,

C 02M e, C O2E t, C0 2 - iso -P r, C 02P r, C_〇 _{2 - cyclo- P r, C O2B} u, C0 2 - sec- Bu, C_〇 ₂ - iso-Bu, C 02 -tert-B, C 0 ₂ — cyc 1 o — Bu, C 02P n, C 0 ₂ — cyc 1 o — P n, C 02P n, C0 ₂ -neo -P n, C0 ₂ -tert -P n , C0 ₂ — H ex, C〇 ₂ — cyclo— H ex, C 0 ₂ -H ep, C 02-0 ct, C 02N (Me) 2, C 02N (E t) 2, C0 ₂ CH ₂ C0 _{2 Me, C0 2 CH 2 C0 2} E t, C O2CH2CO 2 P r, CH2CH (CI) C_〇 _{2 Me, CH2CH (CI) C} O2E t, CH 2 CH 2 C 0 2 Me, CH 2 CH 2 CH 2 C0 ₂ Me, CH2C 0 ₂ Me, CH = CH C〇 ₂ Me CH = CHC0 ₂ E t,

〇 CH ₂ C〇 ₂ Me, 0 CH 2 C 02E t, 0 CH2C O2P r, 0 CH 2 C 02B u, 0 CH2CO2P n, O CH ₂ C0 ₂ H ex, 0 CH ₂ C〇 ₂ -cyc 1 o- P n, 0 CH ₂ C0 ₂ -iso -P r ₍ 0 CH ₂ C 0 ₂ CH ₂ Ph, 0 CH (Me) C 02M e, 0 CH (Me) C O2E t, O CH (Me) CO2P r , oZ

R 3

_{0 CH (Me) C0 2 -} iso- P r, 0 CH (Me) C_〇 _{2 Pn, 0 CH (Me)} CO 2- cyclo- Pn,

S CHsCOzMe, S CH ₂ C0 ₂ E t, SC H2C 0 ₂ P r, SC H2 C O2B u, SC H2 CO 2P n, S CH ₂ C0 ₂ H ex, SCH ₂ C 0 ₂ — cyc 1 o— P n , S CH ₂ C0 ₂ -iso -P r, SCH ₂ C〇 ₂ CH ₂ P h, SCH (Me) C 02Me, S CH (Me) CO 2E t, S CH (Me) CO 2P r, S CH (Me) CO 2- iso - P r, S CH (Me) C_〇 _{2 Pn, S CH (Me)} C0 2 - cyclo- P n,

NH CH 2C 0 ₂ Me, NH CH 2C O 2E t, NH C H2 CO 2P r, NH CH 2 C 0 _Z Bu, NH C H2 CO 2P n, NHCH ₂ C〇 ₂ H ex, NH C H2C O 2 -cyc 1

_{0 -P n, NH CH 2 C0} 2 - iso- P r, NHCH 2 C 02 CH 2 P h, NHCH (Me) C_〇 _{2 Me, NHCH (Me) CO} 2E t, NHCH (Me) C O2P r,

NHCH (Me) C_〇 _{2 - iso- P r, NHCH (} Me) C_〇 _{2 Pn, NHCH (Me) C} 0 2 - cyc 1 o - P n, NH C0 2 Me, NH CO 2E t, NH C 02 P r, NH CO 2- iso -P r, NH C 02B u, NHC_〇 _{2 - cyclo - P r: NH} C0 2 - cyclo- Pn, NHC0 2 - iso- Bu, NHC0 2 - sec- Bu, NH C O2- tert -Bu, NHC 02 CH 2 CH = CHCH 3, NH C 0 2C H 2 CH = CH 2, NHC0 2 CH 2 C≡CH, NH C 02P h, NH CO 2C H2 Ph, NH C O2C H2- (2-Me-Ph), NHCO2CH2- (3-Me-Ph), NHCO2CH2- (4-Me-Ph), NHCO2CH2- (4-Et -P h), NH CO 2CH 2- (2-Me 0 -P h), NH CO 2CH 2- (3-MeO-Ph), NH CO 2C H2- (4 -Me OP h), NH C 02 CH 2- (4-C

1Ph), NH CO 2CH 2-(4-F-Ph), R 3

NH CO 2C H2- (4-CFs-P h), NH CO 2C H2- (2-F-Ph), NHCO 2CH 2- (3-F-P h), NH CO 2CH2- (3—CI—Ph _{), NH C0 2 CH 2 -} (2- CI- Ph), NH CO 2C H2 one (4 -C FaO-Ph), NH SO 2M e, NH S O2E t, NH SO 2P r, NHS 0 2 - iso -P r, NHSO 2B U, NH SO 2C H2P h, NH S O2 CH C 12, NH SO 2 CH 2C 1, NH SO 2C H2C H2C 1, NH SO 2C H2 CH 2C H2C 1, NH SO 2C H2 CF 3, NH S 02P h, N (S O2E t) C 02E t, N (CH ₂ OMe) SO 2E t, N (CH ₂ CH = CH ₂ ) S O2E t, N (CH ₂ C≡CH) SO 2E t, N (Me) S〇 ₂ Me, N (S 0 ₂ Me) ₂ , N (SO 2E t) 2, N (S〇 ₂ Pr) ₂ , N (E t) S 02E t, N (Me ) S 02E t, N (E t) SO 2E t, N (P r) SO 2E t, N (COM e) SO 2E t, N (CH ₂ OMe) S O2M e, N (CH 2O E t) S 0 ₂ Me, N (CHzCH = CH2) S 02 Me, N (CH ₂ C≡CH) S O2M e, C ONH S 0 ₂ Me, C ONH SO 2E t, CONHS〇 ₂ CF ₃ , 1, 3 —Dioxolan-1-yl group, 1,3-dioxane-2-yl group, 4- (1- (ethoxycarbonyl) ethyloxy) phenyloxy Shi group, 4- [1 i (main Tokishikarubo two Le) Echiruokishi] Fueniruokishi group, N (Me) C 02M e , N (CH 2 C≡CH) C O2M e, N (Me) COMe, NHCOMe, NH C 0 P r, N (C H2 C three CH) C OM e, N ( CH 2 C≡CH) C 0 2 M e, N (Me) CO 2C H 2- (4 one CI- Ph), N (CH ₂ C≡ CH) C 02E t, N (CO - tert - B u) S 0 2 M e, N (CO- tert -Bu) SO 2E t, N (2- Me O- Ben Zoiru) S 0 ₂ Me, N (3- M e 0- _{Benzoiru) S 0 2 Me, N (} 4- Me O - Benzoiru) S_〇 _{2 Me, N (2- M e} 0- Benzoiru) S_〇 ₂ E t, N (3- Me O—Benzyl) S 0 ₂ E t, N (4— Me O—Benzyl) S 0 ₂ E t, R 3

C 02- (Okisetan one 3-I _{le), N (CHO) CH 2} C0 2 Me, N (CHO) CH2CO2E t, Ν (CHO) CH (Me) C O2E t, N (COMe) CH2C 02M e, N (COMe) CH (Me) C 02M e, N (CH ₂ C3 N) C 0 ₂ Me: CH = C (CI) C〇 ₂ Me, CH2 C (CI) CO2E t, CH = C (B r ) CO zM e, CH = C (B r) C0 ₂ E t, NHCOC Fa, NHCO CC ls, NH C 0 CF ₂ C 1, NH C 0 CF ₂ H, OC〇 ₂ Me, 0 C O2E t, or N (CH2C ≡N) S 0 ₂ Me

[Table 1 4]

0 O ヽ

N N 'O, N, 0

 R17 R17

To CF ₃ Μ 'N To CF ₃ M'

 N N

R 1 7

R 1 7

Me, E t, P r, iso- P r, B u, sec- B u, iso- B u, C Ha CH = CH2, CH 2 C≡ CH, CH2C≡N, CH2CH2F, CH2CH2C 1, CH 2CH 2 CH ₂ F, CH ₂ 〇Me, CH2O E t, CH ₂ CH ₂ CH ₂ C 1, CH2CH2 CH2CH2F, CH ₂ CC 1 = CH _Z , CH ₂ CB r = CH ₂ , 〇Me, 0 E t, CH ( Me) C three CH, CH (Me) CH two CH ₂ or CH (Me) C≡N Note that symbols in tables represent the following meanings.

Me: CH ₃

E t: CH ₂ CH ₃

P r: CH ₂ CH ₂ CH ₃

iso - P r: CH (CH 3) 2

c y c 1 o -P r: CH (CH2) 2

Bu: CH2CH2CH2CH3

sec—B u: CH (CH ₃ ) C ₂ H 5

iso -B u: CH ₂ CH (CHa) 2

tert -Bu: C (CH ₃ ) ₃

cyclo—B u: CH (CH ₂ ) ₃

Pn: CH2CH2CH2CH2CH3

cyclo -P n: CH (CH ₂ ) ₄

iso -P n: CH ₂ CHzCH (CH ₃ )

cyclo— H ex: CH (CH ₂ ) ₅

H ep: (CH ₂ ) ₆ CH ₃

O ct: (CH ₂ ) 7CH3 P h, Pheny l: C ₆ H ₅

 4— C I one Ph: 4-C I one Phe ny l

 In applying the compound of the present invention as a herbicide, a suitable carrier is generally used, for example, a solid carrier such as clay, talc, bentonite, urea, ammonium sulfate, walnut powder, diatomaceous earth, and white water, water, Alcohols (isopropanol, butanol, ethylene glycol, benzyl alcohol, furfuryl alcohol, etc.), aromatic hydrocarbons (toluene, xylene, methylnaphthalene, etc.), ethers (anisole, etc.) ), Vegetable oils (soy oil, cottonseed oil, etc.), ketones (cyclohexanone, isophorone, etc.), esters (butyl acetate, etc.), acid amides (N-methyl bilolidone, etc.) or halogenated hydrocarbons ( Chlorobenzene etc.), and can be used by mixing with a liquid carrier such as a surfactant. Add emulsifiers, dispersants, penetrants, spreading agents, thickeners, antifreezing agents, anti-caking agents, stabilizers, etc., liquids, emulsions, wettable powders, dry flowables, flowables, powders, granules It can be put to practical use in any dosage form such as an agent.

 In addition, the compound of the present invention may be added to other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil improvement at the time of formulation or application as necessary. It may be mixed and applied with an agent.

 In particular, by mixing and applying other pesticides, it can be expected to reduce costs by reducing the amount of applied chemicals, expand the spectrum by synergistic action of the mixed chemicals, and achieve higher herbicidal effects. At this time, a combination with a plurality of known pesticides is possible at the same time. Examples of the kind of agrochemical used in combination with the compound of the present invention include the compounds described in the 1991 edition of Farm Chemicals Handbook.

 The amount of the applied compound of the present invention may vary depending on the application scene, application time, application method, weather conditions, preparation form, soil conditions, cultivated crops, etc., but generally the amount of the active ingredient is 0 per hectare (ha). 000 1 to 10 kg, preferably 0.001 to 5 kg.

Next, a formulation example of a preparation when the compound of the present invention is used is specifically shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples 'Parts' means parts by weight.

 (Wettable powder)

 Compound of the present invention 0.1 to 80 parts

 Solid carrier ~ 10 to 90 parts

Surfactant 1 to 10 parts

 Other 1-5 copies

 Other examples include an anti-caking agent.

 (Milk)

 Compound of the present invention 0.1 to 30 parts

 Liquid carrier 30 to 9 5 parts

 Surfactant 5 to 15 parts

 (Floable agent)

 Compound of the present invention 0.1 to 70 parts

 Liquid carrier 1 5 to Θ 5 parts

 Surfactant 5 ~ 1 2 parts

 Other 5-30 copies

 Other examples include an antifreezing agent and a viscous agent. [Granular wettable powder (dry flowable agent)]

 Compound of the present invention 0.1 to 90 咅 P Solid carrier 10 to 70 parts

 Surfactant 1-20 parts

 (Granules)

 Compound of the present invention 0.001 to 10 parts Solid carrier 90 to 99.99 99 parts Others 0.1 to 10 parts

 [Formulation Example 1] wettable powder

 Compound of the present invention No. 4 50 parts G-CLIP PFP — 43 parts

(Riki Olin-based clay: J-Client Industries Co., Ltd.) Solpol 50 50 2 parts

 (Anionic surfactant: Toho Chemical Industry Co., Ltd.)

 Lunox 1 000 C-1 ~ 3 copies

 (Anionic surfactant: Toho Chemical Industry Co., Ltd.)

 Curve Rex # 80 (Anticaking agent) ^ ~ 2 parts

 (White carbon: Shionogi & Co., Ltd. product name)

 The above is uniformly mixed and pulverized to obtain a wettable powder.

 [Formulation Example 2] Milk

 Compound of the present invention No. 5 1 3 parts

 Xylene 76 parts

 Isophorone —— — 1 5 parts

 Solpol 300 5 X — 6 parts

 (Mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.)

 The above are uniformly mixed to form an emulsion.

 [Compounding Example 3] Flowable agent

 Compound of the present invention No. 6 35 parts

 AGRISOL S—7 1 1 8 parts

 (Nonionic surfactant: Kao Corporation)

 Lunox 1 000 C 0.5 part

 (Anionic surfactant: Toho Chemical Industry Co., Ltd.)

 20% 1% Rhodepol water

 (增 Glue: Loan 'Poolan brand name)

 Ethylene glycol (antifreeze) 8 parts

 Water 28.5 parts

 The above is uniformly mixed to form a flowable agent.

 [Formulation Example 4] Granular wettable powder (dry flowable)

 Compound of the present invention No. 2 575

Isoban No. 110 (Anionic surfactant: Kuraray Pren Chemical Co., Ltd.) Vanirex N 5 parts

 (Anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd.)

 Curve Rex # 8 0 1 0

 (Which Toka Bon: Shionogi & Co., Ltd. product name)

 The above is uniformly mixed and pulverized to obtain a dry flowable agent.

 [Formulation Example 5] Granules

 Compound of the present invention No. 340.1 parts

 Bentonite 50.0 parts

 Talc 4 4.9 parts

 Toxanone G R— 31 A 5 parts

 (Anionic surfactant: Sanyo Chemical Industry Co., Ltd.)

 After uniformly mixing and grinding the above, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to form granules.

 When used, the above water-dispersible powder, emulsion, floor pull, and granular water-dispersible powder are diluted 50 to 100 times with water to obtain an active ingredient of 0.001 to 1 per hectare (ha). Spray to 0 kg.

 Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples.

 [Test Example 1 1] Herbicidal effect test by weed pre-treatment under flooded conditions

 After putting alluvial soil into the 1/1000 w arena pot, add water and mix to make the water 4 cm deep. Two-leaf rice plants were transplanted into the above pots, and seeds of Nobie, Firefly, Konagi, Kikashigusa, Perica and tubers of Mizugayalli were mixed. Pots are grown in a greenhouse at 25 to 30 ° C and after sowing

On the first day, the compound of the present invention prepared according to the formulation example was treated so as to have a predetermined dose on the water surface. Three weeks after the treatment, the herbicidal effect on various weeds and the effect on rice were visually examined according to the following criteria. 0 is no effect and 5 is a 5-point scale indicating complete withering. The results are shown in Table 5-1.

In each table, N o. Corresponds to the compound N 0. Described in Examples, and symbols are as follows. Show meaning.

 A: Nobie, B: Firefly, C: Konagi, D: Kikasigusa, E: ゥ ヮ, F: Mizugayari, b: Rice

 Judgment criteria

 5 ... 90% or more of weed killing rate (almost completely withered)

 4 ... Weed kill rate 70% or more and less than 90%

 3 ... Weed kill rate 40% or more and less than 70%

 2 ... Weed kill rate 20% or more and less than 40%

 1 ... Weed kill rate 5% or more and less than 20%

 0: Herbicidal rate less than 5% (almost no effect)

 [Test Example-2] Test of herbicidal effect by treatment after weed emergence under flooded conditions

 After putting alluvial soil into the 1/1000 w arena pot, add water and mix to make the water 4 cm deep. The seeds of Novie, Hoyurui, Konagi and Kikasigusa were mixed in the above pots. The pots are grown in a greenhouse at 25 to 30 ° C, and treated with the compound of the present invention prepared according to the formulation so that the potency is at a predetermined level on the water surface 14 days after sowing. did. Three weeks after the treatment, the herbicidal effect on various weeds was visually inspected according to the criteria in Test Example 11. The results are shown in Table 5-2. In each table, No. corresponds to the compound No. described in the examples, and the symbols have the following meanings.

 A: Nobier, B: Hoyu Rui, C: Konagi, D: Kikasigusa

 [Test Example 1-3] Herbicidal effect test by soil treatment

Put the sterilized embankment soil in a 33 cm long, 33 cm wide, 8 cm deep plastic box and place it in nobier, enokologza, oats, blackgrass, ichibi, onnamomi, aobu, asagao, o Mixed seeds of Euonymus aegypti, hakobe, crabgrass, ragweed, agayetou, shiroza, inuyude, maize, rice, wheat, soybean, ivy, beetroot, covered about 1.5 cm, then prescribed dose Thus, the compound of the present invention prepared according to the formulation examples was evenly sprayed on the soil surface. Three weeks after the application of the drug solution, the herbicidal effect on various weeds and the effect on crops were visually inspected according to the criteria in Test Example 11. The results are shown in Table 5-3. In addition, in each table No. corresponds to compound No. described in the examples, and the symbols have the following meanings.

G: Novier, H: Enokorogosa, I: Oatgrass, J: Blackgrass, K: Ichibi, L: Onamomi, M: Aobu, N: Asagao, 0: Ooinoufuguri, P: Hakobe, Q: Mehishiba, R: Buya Kusa, S: Aoga Toto, T: Shiroza, U: Inutade, a: Maize, b: Rice, c: Soybean, d: Tokyu, e: Wheat, f: Beat

 [Test Example 1-4] Test of herbicidal effect by foliage treatment

 Put the sterilized embankment soil in a 33 cm long, 33 cm wide, 8 cm deep plastic box and place it in nobier, enokologza, oats, blackgrass, ichibi, onnamomi, aobu, asagao, o Mixed seeds of Oinufufuguri, Hakobe, Mehishiba, Ragweed, Agaeito, Shiroza, Inuyude, Maize, Rice, Wheat, Soybean, Ivy and Beetroot, After covering about 1.5 cm, 25-3 The plant was grown at room temperature of 0 ° C. for 14 days, and the compound of the present invention prepared according to the formulation example was evenly applied to the foliage so as to have a predetermined dose. Three weeks after the application of the drug solution, the herbicidal effect on various weeds and the effect on crops were visually inspected according to the criteria in Test Example 11. The results are shown in Table 5-4. In each table, No. corresponds to the compound No. described in Examples, and the symbols have the following meanings.

G: Novier, H: Enoko Rogza, I: Oatgrass, J: Blackgrass, K: Ichibi, L: Onamomi, M: Aobu, N: Asagao, 0: Ooinoufuguri, P: Hakobe, Q: Mehishiba, R S: Azagayto, T: Shiroza, U: Inuyu, a: Maize, b: Rice, c: Soybean, d: Touyu, e: Wheat, f: Beat

[Table 5-1] Compound No. Dose g / a A B C D E F b

3 0.64 0 0 5 3 0 0 0

4 0.64 5 5 5 5 5 5 0

5 0.64 5 5 5 5 5 5 0

6 0.64 5 5 5 5 5 5 1

9 0.64 5 5 5 5 5 5 0

1 0 0.64 5 5 5 5 5 5 0

1 1 0.64 5 5 5 5 5 5 1

1 2 0.64 5 5 5 5 5 5 1

1 3 0.64 3 5 5 5 2 0 0

1 4 0.64 3 0 0 0 0 0 0

1 5 0.64 3 3 3 2 0 0 0

1 6 0.64 5 5 5 5 5 5 0

1 7 0.64 4 5 5 5 5 5 0

1 8 0.64 5 5 5 5 5 5 0

1 9 0.64 5 5 5 5 5 5 0

2 1 0.64 5 5 5 5 5 5 0

2 2 0.64 5 5 5 5 5 0

2 3 0.64 5 5 5 5 1 0

2 4 0.64 5 5 5 5 0

2 5 0.64 5 5 5 5 5 5

2 6 0.64 5 5 5 5 5 5

2 7 0.64 5 5 5 5 5 0

2 8 0.64 4 5 5 5 0 0 Compound No. Dose g / a ABCDEF b

2 9 0.64 4 5 5 5 5 0

3 0 0.64 0 5 5 1 0 0

3 1 0.64 5 5 5 5 5 0

3 2 0.64 5 5 5 5 5 0

3 3 0.64 5 5 5 5 5 1 0

3 4 0.64 5 5 5 5 5 5 5

3 5 0.64 5 5 5 5 5 5 0

3 6 0.64 5 5 5 5 5 5 1

3 7 0.64 5 4 5 5 0 0

3 8 0.64 0 0 5 4 0 0 0

3 9 0.64 5 5 5 5 5 5 0

4 0 0.64 5 5 5 5 5 5 1

4 1 0.64 0 3 5 5 5 5 0

4 2 0.64 5 5 5 5 5 5 5

4 3 0.64 5 5 5 5 5 5 0

4 4 0.64 4 1 5 5 2 0 0

4 5 0.64 5 5 5 5 5 5 0

4 6 0.64 5 5 5 5 5 5 0

4 7 0.64 5 5 5 5 5 5 0

4 8 0.64 5 5 5 5 5 5 0

4 9 0.64 5 5 5 5 5 5 0

5 0 0.64 5 5 5 5 5 5 0

5 1 0.64 5 5 5 5 5 5 0 Compound No. Dosage g / a ABCDEF b

5 2 0.64 1 0 5 0

5 3 0.64 5 0 5 0

5 4 0.64 3 5 5 0

5 5 0.64 5 5 5 0

5 6 0.64 5 5 5 0

5 7 0.64 5 5 5 0

5 9 0.64 4 0 5 0

6 0 0.64 5 5 5 0

6 2 0.64 4 0 5 1 0

6 3 0.64 5 5 5 0

6 4 0.64 5 5 5 0

6 5 0.64 5 5 5 0

6 6 0.64 3 5 5 0

[Table 5-2] ィ 匕 物 · ο · Drug dose g / a

2 0.64 3 0 0 0

 "

4 0.64 5 5 5 5

5 0.64 4 3 5 5

6 0.64 5 5 5 5

9 0.64 5 5 5 5

1 0 0.64 5 5 5 5

1 1 0.64 5 5 5 5

1 2 0.64 5 5 5 5

1 3 0.64 0 0 2 4

1 6 0.64 5 5 5 5

1 7 0.64 5 5 5 5

1 8 0.64 5 5 5 5

1 9 0.64 5 5 5 5

2 0 0.64 0 0 4 0

2 1 0.64 5 5 5 5

2 2 0.64 5 5 5 5

2 3 0.64 0 5 5 5

2 4 0.64 0 0 4 5

2 5 0.64 5 5 5 5

2 6 0.64 5 5 5 5

2 7 0.64 3 3 5 5

2 8 0.64 0 2 0 5

2 9 0.64 0 0 5 5 Compound No. Dose g / a ABCD

3 0 0.64 0 1 4 5

3 1 0.64 5 2 5 5

3 2 0.64 5 5 5 5

3 3 0.64 0 5 5 5

3 4 0.64 5 5 5 5

3 5 0.64 5 5 5 5

3 6 0.64 4 5 4 5

3 7 0.64 1 3 3 4

3 8 0.64 3 0 5 2

3 9 0.64 5 5 5 5

4 0 0.64 5 5 5 5

4 1 0.64 0 1 3 5

4 2 0.64 5 5 5 5

4 3 0.64 5 5 5 5

4 4 0.64 0 0 5 0

4 5 0.64 5 5 5 5

4 6 0.64 4 3 4 5

4 7 0.64 5 5 5 5

4 8 2.52 5 5 5 5

4 9 2.52 5 5 5 5

5 0 2.52 5 5 5 5

5 1 0.64 0 5 5 5

5 3 0.64 5 3 5 Compound No. Positive dose g / a ABCD

5 4 0.64 0 5 5

5 5 0.64 5 5 5

5 6 0.64 3 0 0

5 7 0.64 4 3 5

6 0 0.64 0 3 5

6 2 0.64 0 0 5

6 3 0.64 1 0 5

6 4 0.64 5 5 5

6 5 0.64 2 5 5

6 6 0.64 3 5 5

[Table 5-3] Compound No. Dose g / a G H I J K L M N O P Q S T U a b c d e f

2 1.6 0 0 0 0 2 1 2 1 0 0 0 0 0 0 0 0 3 1.6 0 0 0 0 4 1 0 5 4 1 0 0 0 0 0 4 4 1.6 5 5 5 5 1 5 5 5 5 5 5 1 0 1 0 5 5 1.6 5 5 5 5 5 4 5 5 5 5 1 0 1 1 3 5 6 1.6 5 5 3 5 5 5 5 5 5 5 4 5 5 0 1 5 9 1.6 5 5 1 3 5 5 5 5 5 5 1 1 0 4 0 5

1 0 1.6 1 5 3 2 5 1 5 5 5 2 0 0 1 0 0 5 1 1 1.6 5 5 5 4 5 2 5 5 5 5 0 4 0 0 0 5 1 2 1.6 5 5 5 5 5 4 4 5 5 5 5 3 4 2 0 5 5 1 3 1.6 1 5 0 0 5 0 5 0 5 5 0 0 0 0 0 5 1 6 1.6 4 4 2 2 5 5 5 5 5 4 1 0 0 0 0 5 1 7 1.6 3 3 0 0 5 1 5-5 1 0 0 0 0 0 5 1 8 1.6 4 3 1 1 0 5 0 5 3 0 1 0 0 0 2 1 9 1.6 5 5 1 3 5 0 5 0 5 5 1 1 0 0 0 5 2 0 1.6 5 5 0 0 0 0 5 4 1 1 0 0 0 0 0 5 2 1 1.6 5 5 5 5 5 5 5 5 5 5 2 3 3 4 4 5 2 2 1.6 5 5 5 5 5 1 2 4 4 3 1 1 1 0 4 5 2 3 1.6 0 0 0 0 5 0 5 0 0 0 0 0 0 0 0 5 2 4 1.6 2 3 3 1 5 0 3 0 5 5 0 0 0 0 0 5 2 5 1.6 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 2 6 1.6 5 5 5 5 5 3 5 5 5 5 2 4 1 0 2 5 2 7 1.6 3 1 0 0 5 0 5 5 5 0 0 0 0 0 0 5 2 8 1.6 3 1 0 1 5 1 5 3 2 1 0 0 0 0 0 5 Compound No. Dose g / a GHIJKLMNOPQRSTU abcdef

2 9 5 3 1 0 0 0 0 0 5

 6666666666666O 66 666O 666 C

 3 0 3 3 3 0 0 0 0 0 5

 4002 o 320555555555555511

 3 1 4440 32005 δ5555555 δ5555 δ4 5 5 5 3 1 1 4 5

 4400020000 0000555555555

 3 2 4440000000 0203555555511 5 5 5 1 2 1 0 0 5

 444555255555555555 55551

 3 3 04003024 320 555 555 255 511 3 5 0 0 0 0 0 0 5

 0353555555555555555555555 5

 34 5 5 5 5 5 5 5 5 5 3 5 5 5 5 3 5 3 2 3 5 3 6 3 5 5 0 1 0 0 0 5 3 7 0 0 1 0 0 0 0 0 0

3 9 5 5 5 3 3 2 2 5 5

4 0 5 5 5 5 5 4 5 5 5 4 1 0 1 0 0 0 0 0 0 0 4 2 5 5 5 3 5 3 4 5 5 4 3 5 5 5 4 5 3 3 5 5 44 0 0 0 0 0 0 0 0 0 4 5 5 5 5 5 5 3 44 5 4 6 5 5 5 2 1 0 5 0 5 4 7 5 5 5 3 4 2 0 3 3 4 8 4 5 5 1 0 0 0 1 5

4 9 5 5 5 1 2 0 3 0 5

5 0 5 5 5 0 0 0 0 0 5 5 1 5 4 5 0 2 0 5 0 5 5 2 0 1 1 0 0 0 0 0 4 Compound No. Dose g / a GHIJLMNOPQRSTU abcdef

53 1.6 5 4 5 5 5 3 5 5 5 5 1 4 1 1 5 5 54 1.6 0 0 0 0 5 0 5 0 0 0 0 0 0 0 0 5 5 5 1.6 5 3 0 0 1 0 5 0 0 0 1 0 0 0 0 0 56 1.6 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 57 1.6 5 5 5 5 5 1 5 5 5 5 2 5 1 1 4 5 58 1.6 0 5 1 0 5-5 5 4 0 2 0 2 5 0 3

59 1.6 4 0 0-0 0 0 0 3 0 0 0 0 0 0 0

60 1.6 5 5 0 0 5 3 5 4 5 5 0 0 1 1 0 5 6 1 1.6-3-0 5 0 0 5 4 4 5-0-0 0 0 5 62 1.6-0 0 0 0 4 3 0 3 5-0 0-0 0 0 5 63 1.6-0 0 1 5 5 4 0 4--0-0 0 0 3 64 1.6-5 5 5 5 5 5 5 5 5 5 5 2-1 2 4 5 6 5 1.6-5 0 0 5 5 5 5 5 5 5 0 1-1 1 0 5 66 1.6-0 0 0 5 5 5 3 2 2-0-0 0 0 5

[Table 5-4] Compound No. Dose g / a G H I J L M N O P Q R S T U a b c d e f

1 1.6 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 2 1.6 0 0 0 0 5 1 5 4 0 0 0 0 0 0 0 0 3 1.6 0 1 0 1 5 2 4 4 5 4 0 0 0 0 0 3 4 1.6 4 4 5 5 5 5 5 5 5 5 1 2 0 1 4 5 5 1.6 3 3 1 5 5 5 5 5 5 5 0 0 2 1 0 4 6 1.6 5 5 3 5 5 5 5 5 5 5 2 2 5 1 2 5 9 1.6 5 5 1 5 5 5 5 5 5 5 2 1 1 5 0 5

1 0 1.6 4 5 1 3 5 5 5 5 5 5 1 0 4 5 1 5 1 1 1.6 5 5 5 5 5 5 5 5 5 5 3 1 5 5 2 5 1 2 1.6 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 1 3 1.6 2 5 1 2 5 5 5 5 5 5 1 0 2 1 0 5 1 4 1.6 0 0 0 0 1 2 5 3 0 0 0 0 0 0 0 0 1 5 1.6 3 1 0 1 5 2 5 5 5 0 0 0 0 5 0 5 1 6 1.6 3 3 2 5 5 5 5 5 5 5 2 0 1 5 0 5 1 7 1.6 3 5 2 5 5 5 5 5 5 5 1 0 1 5 0 5 1 8 1.6 5 4 4 4 5 5 5 5 5 5 2 3 2 5 1 5 1 9 1.6 3 5 5 4 5 5 5 5 5 5 3 2 4 5 1 5 2 0 1.6 3 3 1 1 5 5 5 5 5 5 1 0 1 5 0 5 2 1 1.6 5 5 5 5 5 5 5 5 5 5 1 3 5 5 3 5 2 2 1.6 5 5 4 3 5 5 5 5 5 5 1 1 3 5 3 5 2 3 1.6 5 5 1 1 5 5 5 5 5 1 1 0 1 5 0 5 2 4 1.6 2 5 1 2 5 5 5 5 5 5 1 0 1 5 0 5 2 5 1.6 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 Compound No. Dose g / a GHIJKLMNOPQRSTU abcdef

2 6 1.6 5 5 5 5 5 5 5 5 5 5 4 4 5 5 3 5 2 7 1.6 5 5 3 3 5 5 4 5 5 5 1 0 5 5 0 5 2 8 1.6 3 3 1 1 5 5 5 5 5 5 1 0 0 5 0 5

2 9 1.6 1 2 2 5 5 5 5 5 5 1 0 0 5 0 5

3 0 1.6 0 3 0 1 5 0 1 2 2 2 0 0 0 0 0 5 3 1 1.6 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 3 2 1.6 5 5 1 4 5 5 5 5 5 5 3 4 2 1 2 5 3 3 1.6 5 5 2 1 5 5 5 5 5 5 0 0 1 5 0 4 3 4 1.6 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 3 5 1.6 5 5 5 4 5 5 5 5 5 5 2 2 4 5 5 5 3 6 1.6 4 5 2 5 5 5 5 5 5 5 1 1 1 5 0 5 3 7 1.6 1 1 1 1 5 3 5 5 5 5 0 0 1 4 0 5 3 8 1.6 1 1 1 0 3 1 1 1 3 2 0 0 1 0 0 0

3 9 1.6 5 5 3 5 5 5 5 5 5 5 5 5 5 5 5 5 5

4 0 1.6 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 4 1 1.6 0 4-1 5 1 1 1 5 0 0 1 0 0 1 4 2 1.6 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 3 1.6 5 5 4 5 5 5 5 5 5 5 3 5 5 5 5 5 44 1.6 1 1 0 0 5 5 1 3 2 1 0 0 0 0 0 1 4 5 1.6 5 5 5 5 5 5 5 5 5 5 3 4 5 5 5 5 4 6 1.6 4 4 3 5 5 5 5 3 5 5 1 0 0 5 0 5 4 7 1.6 5 5 4 5 5 5 5 5 5 5 3 5 5 5 2 5 4 8 1.6 4 5 3 3 5 5 5 5 5 5 1 1 3 5 1 5 Compound No. Dose g / a GHIJKLMNOPQRSTU abcdef

4 9 1.6 5 5 1 3 5 5 5 5 5 5 1 0 0 5 0 5

5 0 1.6 1 3 1 3 5 5 5 3 5 5 0 0 0 5 0 5 5 1 1.6 1 3 0 2 5 5 5 3 5 5 0 0 0 5 0 5 5 2 1.6 0 0 0 0 4 0 2 1 4 1 0 0 0 0 0 0 5 3 1.6 4 4 4 5 5 5 5 5 5 5 2 2 2 2 3 5 5 4 1.6 0 0 2 0 5 5 4 5 5 5 0 0 1 5 0 5 5 5 1.6 2 2 0 0 5 1 5 1 5 0 1 0 0 3 2 5 5 6 1.6 0 0 1 0 3 1 5 0 5 0 0 0 0 0 0 0 5 7 1.6 4 5 3 5 5 3 3 4 5 4 4 1 1 1 2 5 5 8 1.6 0 0 0 0 5 5 0 5 5 0 0 0 0 0 0 1

5 9 1.6 4 1 0 1 5 3 0 0 5 5 0 0 0 0 0 0

6 0 1.6 0 0 1 1 5 5 1 3 5 5 0 0 1 1 0 5 6 1 1.6-0 0 0 4 5 0 0 0 3--0-0 0 0 4 6 2 1.6-1 5 4 5 5 5 1 5 5--0-2 5 1 5 6 3 1.6-3 2 1 5 5 5 0 5 5--1-1 5 0 5 6 4 1.6-5 3 5 5 5 5 5 5 5 5 5 1-1 5 4 5 6 5 1.6-5 2 5 5 5 5 5 5 5 5 5 0-2 5 0 5 6 6 1.6-2 0 0 4 2 2 2 1 5-5 0-1 0 0 1

Claims

'' ^  1. Equation (1)

[Where R f is C! Represents one C ₄ haloalkyl group,  X and Y each independently represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, X~Y is N = N, C (R a ) = C (R b) (Ra, Rb it it independently water atom, a halogen atom, d-C ₄ alkyl group, C -! C ₄ alkoxy group , d-C ₄ haloalkyl group, a hydroxyl group, an amino group, a mercapto group, a carboxyl group, human Doroki Shimechiru group, forces Rubamoiru group, a formyl group, CC ₄ alkylcarbonyl group, C! over C ₄ alkoxycarbonyl group, C! over C ₄ alkylamino group, C ₂ - Cs alkenyl le group, C ₂ - C ₆ alkynyl group, CC ₄ alkylmercapto helmet group, C ₃ - C ₆ alkenyl Niruamino group, C ₃ - C ₆ Arukiniruamino group, Benjiruokishi group, Benzylamino, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, pyridyl or optionally substituted phenyl (SP1) group (optionally substituted phenyl (SP1 ) Group is a halogen atom, c! — C ₄ alkyl group, d-c ₄ § alkoxy group, C i-C ₄ represents a haloalkyl group, a C c ₄ haloalkoxy groups, or phenylene Le optionally substituted by a group phenylene Le group).),  C (Ra) = N (Ra represents the same meaning as described above.), N = C (Ra) (Ra represents the same meaning as described above.), CH (Ra) CH (Rb) (Ra and Rb have the same meanings as described above.) 1 Π8  WO 98/14452 PCT / JP97 / 03524 _{CH2CH2CH2, CH = CHCH 2, CH} 2 CH = CH,  NH C (R a) R b (R a and R b represent the same meaning as described above.)  C (R a) (R b) NH (R a and R b have the same meanings as described above.), C (= 0) C (= 0), CH 2 C (= 0) NH, CH 2 CH 2 S0 2,  C (= 0) CH (Ra) (Ra represents the same meaning as described above.),  CH (Ra) C (= 0) (Ra represents the same meaning as described above.),  C (= 0) NH, C (= S) NH, NH C (= 0), NH C (= S),  C (= 0) C (Ra) = N (Ra represents the same meaning as described above.),  C (= 0) C (R a) = C (R b) (R a and R b have the same meanings as described above.)  C (R a) = C (Rb) C (= 0) (R a and R b have the same meanings as described above.)  N = C (Ra) C (= 0) (Ra represents the same meaning as described above.) CH (Ra) C (= 0) NH (Ra represents the same meaning as described above), C (= 0) N (Ra) C (= 0) (Ra represents the same meaning as described above.) C (R a) = N C (= 0) (R a has the same meaning as described above.) C (Ra) 0 (Ra represents the same meaning as described above.), Represents C (= 0) 0, 0 C (= 0) or S C (= 0),  A represents a nitrogen atom or CH, Z is an oxygen atom, a sulfur atom, NR c (R c is a hydrogen atom, d—C ₄ alkyl group, C! —C ₄ alkoxycarbonyl group, C 1 -C ₄ alkoxycarbonylmethyl group or phenyl which may be substituted (SP 2) group (optionally substituted phenyl (SP 2) group means a halogen atom, d—C ₄ alkyl group, d—C ₄ alkoxy group or C, —C 4 haloalkyl group Or NNHR c (R c has the same meaning as described above.) R g represents a hydrogen atom, a halogen atom, a cyano group, a C i -C ₄ alkoxycarbonyl group, a C 3 -C ₆ alkenyl group, a C 3 -C ₆ alkynyl group or a C! -C 4 alkyl group; R1, R2, R3, R4 and R5 each independently represent a hydrogen atom, a halogen atom , Nitro, cyano, thiocarbamoyl, carbamoyl, mercapto, hydroxy, amino, formyl, carboxyl, vinyl, ethynyl, trimethylsilylethynyl, cyanomethyl, sulfamoyl group, C -! C ₈ alkyl group, C ₃ - C ₈ alkenyl group, CC 4 alkylsulfonyl group, c ₃ - C ₈ alkynyl group, C3-C8 cycloalkyl group, C C4 haloalkyl group, C3-C ₈ haloalkenyl group, C 3- C 8 haloalkynyl group, d-C ₄ Ashiru group, C l one C 4 § alkoxy (c -! C ₂₎ alkyl group, c, one c ₄ alkylsulfinyl group, substituted Tei Phenyl (SP 3) group (optionally substituted phenyl (SP 3) group is a halogen atom, a C! -C ₄ haloalkyl group, a d-C alkyl group, a C! -C alkoxy group, CC 4 haloalkoxy group, methanesulfonyl group, 1 C ₄ alkoxycarbonyl group, a nitro group, arsenate Dorokishiru group, an amino group, Shiano group one 〇 represents an _{CH (CH 3) C 02 (} d- C 4 alkyl) group or a _{0- CH 2 C 0 2 (C} i- C 4 alkyl) Good phenylene Le group optionally substituted by group. ), — Q— (Optionally substituted phenyl (SP 3) group) group (Q represents a saturated or unsaturated, branched, optionally substituted halogen atom, C Ce alkylene chain; The optionally substituted phenyl (SP 3) group has the same meaning as described above.), A 10-Q— (optionally substituted phenyl (SP 3) group) group (Q and the optionally substituted phenyl (SP 3) group have the same meanings as described above.), —S—Q— (optionally substituted phenyl (SP 3) group) group (Q and And the optionally substituted phenyl (SP 3) group have the same meaning as described above.), -NH-Q- (optionally substituted phenyl (SP 3) group) group (Q and The phenyl (SP 3) group which may be substituted has the same meaning as described above.), And the phenyl (SP 3) group which may be substituted (phenyl (SP 3) which may be substituted) ) Group has the same meaning as described above.), 一 S— (optionally substituted phenyl (SP 3) group) group (optionally substituted phenyl (SP 3) group has the same meaning as described above) ), One NH— (an optionally substituted phenyl (SP 3) group) (optionally substituted phenyl (SP 3) group has the same meaning as described above), -0-R 11 (R 11 is a CC ₈ alkyl group, C ₃ —〇 ₈ cycloalkyl group, C ₃ —C ₈ cycloalkyl (C! — C alkyl, c ₃ —c ₈ alkenyl, C ₃ —C ₈ alkynyl, C ₃ —C ₈ haloalkenyl, C 1 -c ₄ noloalkylcarbonyl, C ₃ —C ₈ no, alkynyl group of mouth, C 1 -C 4 haloalkyl group, C! — C 4 alkoxy (C .- represent C ₄₎ alkyl group, Shianomechiru group or C c ₄ Ashiru group. ), One NH-R 11 (R 11 has the same meaning as described above.), One S—R ll (R 11 has the same meaning as described above.), —CON (d—Ca alkyl ) ₂ groups, — CONH (C! -C ₄ alkyl) group, — C〇 ₂ R 12 (R 12 is C! — C ₈ alkyl group, C ₃ — C ₈ cycloalkyl group, C ₃ — C ₈₎ An alkenyl group, a C ₃ -C ₈ alkynyl group, an optionally substituted phenyl (SP 3) group (an optionally substituted phenyl (SP 3) group has the same meaning as described above), —Q — (Optionally substituted phenyl (SP 3) group) (Q and optionally substituted phenyl (SP 3) group have the same meanings as described above.), Oxetane-3-yl group, C, —C ₄ alkoxycarbonylmethyl group Or (d-C alkyl) _2- amino group. ), One CO NH R 1 2 (R 1 2 represents the same meaning as above.) One _{Q- C 0 2 R 1 2 (} Q and R 1 2 represents the same meaning as above.) One 0—Q—C 0 ₂ R 12 (Q and R 12 have the same meanings as above.), —NH—Q—C〇 ₂ R 12 (Q and R 12 have the same meanings as above.) :), — S— Q— C 0 ₂ R 12 (Q and R 12 have the same meanings as above.), — NH S〇 ₂ R 13 (R 13 is C! — Represents a C ₈ alkyl group, a C 1 -C 4 haloalkyl group, a C 3 -C ₆ cycloalkyl group, a C ₃ -C ₈ alkenyl group, a C ₃ -C ₈ alkynyl group, a benzyl group or a phenyl group. , One N (SO ₂ R 13) 2 (R 13 has the same meaning as described above.), One C〇NH S 0 ₂ R 14 (R 1 4 is C -! CA alkyl group, or a C, -. The Cw, representing the mouth alkyl group), one N (R 1 5) S 0 2 R 1 3 (R 1 3 represents the same meaning as defined above , R 15 is a C! —C ₆ alkyl group, a C ₃ —C ₈ alkenyl group, a C ₃ —C ₈ alkynyl group, a C _t —C 4 haloalkyl group, a C ₃ —C ₈ no, a loalkenyl group, a C 3 — C ₈ hacoalkynyl group, C t— C sacyl group, formyl group, cyano (d—C4) alkyl group, d—C 4 alkoxy (C 1 -C ₄ ) alkyl group, CC! Alkoxycarbonyl group or 1 C (= 0) (optionally substituted phenyl (SP 3) group) group (optionally substituted phenyl (SP 3 ) Represents the same meaning as described above. ), — NH C 0 ₂ R 1 6 (R 1 6 is C one C ₆ alkyl group, C ₃ -C ₈ alkenyl group, C ₃ -!! C ₈ alkynyl group, C over C ₄ haloalkyl group, phenyl group or a Q-(substituted Optionally substituted phenyl (SP 3) group (Q and the optionally substituted phenyl (SP 3) group have the same meanings as described above. :)), 10-C〇 ₂ R 1 6 (R 1 6 represents the same meaning as above.), one _{N (R 1 5) C0 2} R 1 6 (R 1 5, R 1 6 represents the same meaning as above;.), 1 N (R 15) R 11 (R 11 and R 15 have the same meanings as described above.), 2,3-epoxy-2-methylpropyl group, 2-methyl-12-propenyl A 1,3-dioxolan-12-yl group or a 1,3-dioxane-12-yl group; R 2 and R 3 form a heterocycle as shown in formulas (a), (b) and (c) to form <,

In the formulas (a), (b) and (c), R f, R g, A, X, Y, Z, R l, R 4 and R 5 represent the same meaning as described above, R 17 is a CC ₆ alkyl group, a C ₃ -C ₈ alkenyl group, a C ₃ -C ₈ alkynyl group, a CC ₄ haloalkyl group, a C 3 -C 8 noloalkenyl group, a C 3 -C 8 alkynyl group, a C 3 t-C ₆ Ashiru group, a formyl group, Benzoiru group, C i-C ₆ Bruno, mouth alkyl Cal Boniru group, Fuenashiru group, C ₃ - C ₈ cycloalkyl (C -! C ₄₎ alkyl group, C! -. 4 alkoxy (C t-C ₄₎ alkyl _{group, - Q- C 0 2 (C} 1 - C 4) alkyl group (. However, Q represents the same meanings as defined above) one Q-CN group (wherein, Q Represents the same meaning as described above.) Or one Q— (optionally substituted phenyl (SP 3) A group) wherein Q and a phenyl (SP 3) group which may be substituted have the same meaning as described above;  However, when these compounds include optical isomers, diastereomers, and geometric isomers, both the mixtures thereof and the isolated isomers are included. ] The compound shown by these, and its salt. 2. [R f according to claim 1 represents a C! —C ₄ haloalkyl group;  X and Y each independently represent a carbon, nitrogen, oxygen or sulfur atom; X~Y is N = N, C (R a ) = C (R b) (Ra, Rb it it independently water atom, a halogen atom, Ct one C ₄ alkyl group, d-C ₄ alkoxy group, d—C ₄ haloalkyl group, hydroxyl group, amino group, mercapto group, carboxyl group, hydroxymethyl group, carbamoyl group, formyl group, CC 4 alkylcarbonyl group, C i—C ₄ alkoxycarbonyl group, CC ₄ alkylamino group , C ₂ - C ₆ alkenyl Le group, C ₂ - C ₆ alkynyl group, C 1-C ₄ alkylmercapto helmet group, C ₃ - C ₆ alkenyl Niruamino group, C ₃ -C ₆ Arukiniruamino group, Benjiruokishi group, Benzylamino group, CC 4 alkylsulfinyl group, C! -C 4 alkylsulfonyl group, pyridyl group or optionally substituted phenyl (SP 1) group (optionally substituted phenyl (SP 1) group Is a halogen atom, C, — c ₄ al Kill group, C i one c ₄ § alkoxy group, c -! C ₄ haloalkyl group, c, - c represents a ₄ Hakoarukokishi group or phenylene Le Good phenylene Le group optionally substituted by group). ),  C (Ra) = N (Ra represents the same meaning as described above.),  N = C (R a) (Ra represents the same meaning as described above.),  CH (Ra) CH (Rb) (Ra and Rb have the same meanings as described above.), _{CH2CH2CH2, CH = CHCH 2, CH} 2 CH = CH,  NH C (Ra) Rb (Ra and Rb represent the same meaning as described above.)  C (Ra) (Rb) NH (Ra and Rb have the same meanings as described above.), C (= 0) C (= 0), CH ₂ C (= 0) NH, CH2CH2S O2,  C (= 0) CH (Ra) (Ra represents the same meaning as described above), CH (Ra) C (= 0) (Ra represents the same meaning as described above), C (= 0) NH, C (= S) NH, NHC (= 0), NHC (= S),  C (= 0) C (Ra) = N (Ra represents the same meaning as described above.)  C (= 0) C (Ra) = C (Rb) (Ra and Rb represent the same meaning as described above.)  C (Ra) = C (Rb) C (= 0) (Ra and Rb have the same meanings as described above.)  N = C (Ra) C (= ◦) (Ra represents the same meaning as described above.), CH (Ra) C (20) NH (Ra represents the same meaning as described above.), C (= 0) N (Ra) C (= 〇) (Ra represents the same meaning as described above.), C (Ra) = NC (= 0) (Ra has the same meaning as described above.) ), C (R a) 0 (R a has the same meaning as described above.), C (= 0) 0, 0 C (= 0) or S C (= 0),  A represents a nitrogen atom or CH, Z is an oxygen atom, a sulfur atom, NR c (R c is a hydrogen atom, d—C ₄ alkyl group, C! —C ₄ alkoxycarbonyl group, C i—C ₄ alkoxycarbonylmethyl group or phenyl which may be substituted (SP 2) group (optionally substituted phenyl (SP 2) group means a halogen atom, d—C ₄ alkyl group, d—C ₄ alkoxy group or C! —C 4 haloalkyl group. NNHR c (R c has the same meaning as described above.) R g is a hydrogen atom, a halogen atom, Shiano group, CC ₄ alkoxycarbonyl group, C 3- C ₆ alkenyl group, C 3- C 6 alkynyl or C -! A C ₄ alkyl group and Table Wa,  R 1 represents a hydrogen atom or a halogen atom,  R 5 represents a hydrogen atom or a halogen atom, R 2 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a thiocarbamoyl group, a carbamoyl group, a mercapto group, a hydroxyl group, an amino group, a formyl group, a carboxyl group, a vinyl group, a ethynyl group, and a trimethylsilyl group Echiniru group, Shianomechi group, a sulfamoyl group, phenyl group, benzyl group, C i one C ₈ alkyl group, C ₃ - C ₈ alkenyl group, C ₃ - C ₈ alkynyl group, C!ー C ₄ hacoalkyl group, d-C Alkoxy group, C 1 -C ₄ noroalkoxy group, C ₃ -C ₈ haloalkenyl group, c ₃ -c ₈ haloalkynyl group, C i -C 4 acyl group, C 1 -C 4 alkylsulfonyl group, C t — C 4 alkylthio groups, d—C ₄ alkoxy (d—C ₂ ) alkyl groups, 1 C〇2 (C 1- C ₄ alkyl) group, - C_〇_N (d-C 4 alkyl) ₂ group, - C ONH (d-C ₄ § alkyl) group, one NH- (d-C alkyl) group, -N (C 1 - C ₄ alkyl) ₂ group, -O- CH2C O2 (C -! CA alkyl) _{group, - S- C 0 2 (d-} C 4 alkyl) _{group, -NH CH 2 C 0 2 (} C -! CA alkyl) Group or 10—Q— (optionally substituted phenyl (SP 3) group) group (however, Q may be branched, saturated or unsaturated, and may be substituted with a halogen atom. A phenyl (SP 3) group, which represents a C 6 alkylene chain, and which may be substituted, includes a halogen atom, a C, —C ₄ haloalkyl group, a d—C ₄ alkyl group, a d—C 4 alkoxy group, a C! one C, Roarukoki sheet group, methanesulfonyl group, C i one C 4 alkoxycarbonyl group, a nitro group, human de port hexyl group, an amino group, Shiano group, one 0- CH (CHs) C O2 ( d- C 4 A Ruki Le) represents a group or one hundred and one CH ₂ C 0 ₂ (d- C alkyl) Good phenylene Le group optionally substituted by group.) Represent, R 3 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a thiocarbamoyl group, a carbamoyl group, a mercapto group, a hydroxyl group, an amino group, a formyl group, a carboxyl group, a vinyl group, a ethynyl group, a cyanomethyl group, a sulfamoyl group group, d one C ₈ alkyl group, C ₃ - C ₈ alkenyl group, C C'i alkylsulfonyl group, Cs — C ₈ alkynyl group, C 3 — C 8 cycloalkyl group, C, 1 C 4 haloalkyl group, C ₃ -1C 8 haloalkenyl group, C 3 — C 8 noloalkynyl group, C 1 — C 4 acyl group, d — C ₄ alkoxy (c, — c ₂ ) alkyl group, c! — C ₄ alkylsulfinyl group, phenyl (SP 3) group which may be substituted (however, phenyl (SP 3) group which may be substituted halogen atoms and, C, one C ₄ haloalkyl groups, C -! C ₄ alkyl group, one C 4 alkoxy groups, C [one c ₄ haloalkoxy group, a methanesulfonyl group, c ₄ alkoxycarbonyl group, a nitro group, human Dorokishiru group, an amino group, Shiano group, one _{0- CH (CH 3) C O2} (d- C 4 alkyl) group or a 0- CH ₂ C 0 ₂ - optionally substituted by (C! C alkyl) group Represents a good phenyl group.), -Q- (optionally substituted phenyl (SP 3) group Groups (Q and substituted 1 in  WO 98/14452 PCT / JP97 / 03524 The radical (SP 3) has the same meaning as described above. ), 10-Q- (optionally substituted phenyl (SP 3) group) group (Q and optionally substituted phenyl (SP 3) group have the same meanings as described above), 1 S — Q— (optionally substituted phenyl (SP 3) group) group (Q and optionally substituted phenyl (SP 3) group have the same meanings as described above), and one NH—Q— (Optionally substituted phenyl (SP 3) group) group (Q and optionally substituted phenyl (SP 3) group have the same meanings as described above.), — 0— (substituted Phenyl (SP 3) group (optionally substituted phenyl (SP 3) group has the same meaning as described above.), One S— (optionally substituted phenyl (SP 3) 3) group) group (optionally substituted phenyl (SP 3) group has the same meaning as described above) or — NH— (optionally substituted phenyl (SP 3) group) (optionally substituted phenyl (SP 3) group has the same meaning as described above); -0-R 11 (R 11 is a CC ₈ alkyl group, a C ₃ -C ₈ cycloalkyl group, a C ₃ -Ce cycloalkyl (CC ₄ ) alkyl group, a C ₃ -C ₈ alkenyl group, a C ₃ -C ₈ alkynyl group, — C ₈ haloalkenyl group, C haloalkylcarbonyl group, c ₃ — c ₈ haloalkynyl group, C, -C ₄ haloalkyl group, C! — C4 alkoxy (CC ₄ ) alkyl group, cyanomethyl group or CC ₄ Represents an acyl group. ), One NH-R 11 (R 11 has the same meaning as described above;;), —S—R ll (R 11 has the same meaning as described above. :), —C 0 ₂ R 12 ( R 12 is d—C ₈ alkyl group, C ₃ —C ₈ cycloalkyl group, C ₃ —C ₈ alkenyl group, C ₃ —C ₈ alkynyl group, oxetane-13-yl group, CC 4 alkoxycarbonylmethyl Represents a group, (d—C ₄ alkyl) ₂ amino group, phenyl group or benzyl group.), — C ONHR 12 (R 12 has the same meaning as described above;;), 1—Q—C〇 ₂ R 12 (Q and R 12 have the same meanings as described above), — 0—Q—C 0 ₂ R 12 (Q and R 12 have the same meanings as described above), — NH—Q—C0 ₂ R 12 (Q and R 12 have the same meanings as above), and S—Q—C 0 ₂ R 12 (Q and R 12 have the same meanings as above.) represent;.), - NH S 0 2 R 1 3 (R 1 3 is CC ₈ alkyl groups, C C ^ haloalkyl groups, C ₃ - C ₆ cycloalkyl groups, C ₃ - C ₈ alkenyl groups, C ₃ — C _{8 It represents} alkynyl, benzyl or phenyl. ), N (S〇 ₂ R 13) 2 (R 13 has the same meaning as described above.), —CONH S 0 ₂ R 14 (R 14 is a C t -C ₄ alkyl group or C ! represent over C ₄ haloalkyl group.), one N (R 1 5) S 0 2 R 1 3 (R 1 3 represents the same meaning as above,! ^丄Haji! one. beta alkyl, C3- C 8 alkenyl group, C 3—C 8 alkynyl group, Cl—C 4 haloalkyl group, C ₃ —C ₈ noloalkenyl group, C ₃ —C ₈ haloalkynyl group, C! —Cs acyl group, formyl group , Shiano (C -! C) alkyl, d-C ₄ alkoxy (d-C ₄₎ alkyl group, c _t one C ₄ alkoxycarbonyl group or a C (= 0) (optionally substituted phenyl ( SP 3) group) group (which may be substituted phenylene Le (SP 3) group represents represents) the same meaning as _{above), -.. NHC0 2 R} 1 6 (R 1 6 is C , ー C ₆ alkyl group, C ₃ — C ₈ alkenyl Group, C ₃ -C ₈ alkynyl group, CC ₄ haloalkyl group, phenyl group or —Q— (optionally substituted phenyl (SP 3) group) group (Q and optionally substituted phenyl (SP 3 ) group represents represents) the same meaning as _{above), - 0- C0 2 R 1} 6 (R 1 6 represents the same meaning as above;...), one N (R 1 5) C 0 ₂ R 16 (R 15 and R 16 have the same meanings as described above.) Or —N (R 15) R 11 (R 11 and R 15 have the same meanings as described above.) ),  R 4 is a 2,3-epoxy-2-methylpropyl group, a hydrogen atom, a 2-methyl-2-propenyl group, a halogen atom, a 1,3-dioxolan-1-yl group or a 1,3-dioxane Represents a 2-yl group; R 2 and R 3 may form a heterocycle as shown in formulas (a), (b) and (c),

Incidentally, R f, Rg, A, X, Y, Z, R l, R 4 and R 5 in the formulas (a), (b) and (c) represent the same meaning as described above, R 17 is a CC ₆ alkyl group, a C ₃ -C ₈ alkenyl group, a C ₃ -C ₈ alkynyl group, a C 1 -C ₄ haloalkyl group, a C — C nodoloalkenyl group, a C ₃ —Cs haloalkynyl group, a C i — C ₆ acyl group, formyl group, benzoyl group, C! One C ₆ C port alkyl Cal Boniru group, Fuenashiru group, C ₃ - C ₈ cycloalkyl (d-C alkyl, C -. Alkoxy (d-C ₄₎ alkyl group, one Q- C0 ₂ (CC ₄₎ alkyl Group (however, Q represents the same meaning as described above.) One Q—CN group (however, Q represents the same meaning as above.) Or —Q— (optionally substituted phenyl (SP 3 (Wherein Q and the optionally substituted phenyl (SP 3) group have the same meaning as described above.)] And a salt thereof. 3. R f according to claim 1 is CF ₃ group, R g is hydrogen atom, Z is oxygen atom, R 1 is water A compound represented by a hydrogen atom or a halogen atom, R 5 by a hydrogen atom or a halogen atom, R 2 by a halogen atom, a nitro group, a cyano group or a thiocalbamoyl group.  4. The compound according to claim 1, wherein A represents a nitrogen atom, and X to Y are represented by CH = CH. 5. R 3 according to claim 1 is -OR ll, — C〇 ₂ R 12, -Q-C 0 ₂ R 12, -OQ-CO 2R 1 2, -SQ-CO 2R 1 2,1-NHS0 _{2 R 1 3, -N (R} 1 5) S 0 2 R 1 3 or a NH C0 ₂ R 1 compound represented by 6.  6. A herbicide comprising the compound according to claim 1.